Categories
Financial Planning Military Pay Taxes

Avoiding Tax Season Panic: Practical Tips for Tax Planning and Less Stress!

 

 

Tax season has been over for a few months and the panic is over.  Now’s the perfect time to gain a better handle on your tax situation with some tax planning. Have you withheld enough tax? Are you secretly hoping that the IRS has a “we’ve got your back” program? Spoiler alert: they don’t! Here are some practical tips to get you started:

Step 1: Find Out If You’re on Track

Before you can make any plans, you need to know where you stand. Generally, an underpayment penalty can be avoided if you use the safe harbor rule for payments described below. The IRS will not charge you an underpayment penalty if you pay the lesser of 90% of this year’s tax liability or 100% (or 110% for high earners) of the previous year’s tax liability. Your state may have different rules, so be sure to check those as well.

Free Resources

Step 2: Make a Plan

Once you know where you stand, it’s time to make a plan.

  • Earmark funds for an upcoming tax bill in a high-yield savings account (or cash equivalent fund) for flexibility. This allows you to earn a little interest while you wait. 
  • Avoid investing these funds in the stock market for short-term needs.
  • Make adjustments to any withholding for a more “glide slope” approach to paying your tax liability.

Step 3: Monitor Changes Throughout the Year

Your financial situation isn’t static; things change, and so should your tax strategy.

  • Regularly review your income and expenses to adjust your tax strategy as needed.
  • Revisit your withholding if you start generating income from a rental property or a side hustle to avoid surprises at tax time.

Finding the Right Professional

Feeling motivated to do some tax planning but that’s not how you want to spend your Saturday night? (Because who wouldn’t want to spend their free time in a thrilling game of tax chess with the IRS as your opponent?) Should you reach out to a tax professional, a financial planner, or both? Let’s break down what each one does:

  • Tax Professionals: These include CPAs, Enrolled Agents, and Tax Preparers. They are equipped to file your taxes, represent you in tax court, and help you navigate complex tax issues. If you have specific tax questions or need assistance filing, they’re your go-to experts.
  • Financial Planners: These professionals help you strategize for future taxes and financial goals, such as retirement. They can provide guidance on how to manage your investments and income to minimize your tax burden. A good financial planner will review your overall financial picture and help you plan for future tax obligations.

When to Seek Help and Who to Reach Out To

It’s highly encouraged that you reach out to one of the above professionals if you:

  • Haven’t Filed Taxes in a Few Years: You need someone who can prepare your taxes so this is where the tax professionals could help you out. 
  • Owe Money or Are Receiving Large Refunds: Owing money opens you up to potential penalties, while a large refund means you’re giving the government an interest-free loan for the year. A financial planner can help you review your income and expenses to prepare tax projections and recommend changes.
  • Received a Notice from the IRS or State Revenue Agency: A tax professional can assist in communication with the appropriate agency.
  • Are Transitioning Out of the Military: Work with a financial planner to navigate your potential state tax bill.
  • Started a Side Hustle: A tax professional can help set up automatic payments, while a financial planner can assist with calculating quarterly payments.
  • Are Turning Your Primary Residence into a Rental Property: This can complicate your tax situation, as you’ll need to account for rental income and potential deductions. A financial planner can help you see how this change will affect your overall financial picture (should you sell instead?). A tax professional can help during tax time by ensuring you maximize your deductions and comply with tax laws.

Tax planning doesn’t have to be a daunting task. By taking proactive steps and consulting the right professionals, you can make the process smoother and more manageable. Whether you’re preparing for a rental income, transitioning out of the military, or simply trying to understand your tax situation better, there are resources available to help you. The financial planners at the Military Financial Advisors Association are here to help! 

This blog is provided for educational purposes and is not intended as individual investment or tax advice.

Categories
Estate Planning Taxes

529 ABLE Accounts and Veteran Eligibility: Big Changes for 2026

I’ve been asked by disabled veterans many times whether they qualify for an ABLE account, formally known as a 529 ABLE plan. Until now, my answer has often been no; not because their disabilities weren’t real or significant, but because the rules required that the qualifying disability begin before age 26. That restriction excluded many servicemembers whose disabilities occurred later in life. Beginning in 2026, that changes in a meaningful way thanks to the ABLE Age Adjustment Act.

What Is an ABLE Account?

The original Achieving a Better Life Experience (ABLE) Act was designed to allow individuals with disabilities to save money without putting essential benefits at risk. ABLE accounts are modeled after 529 college savings plans and offer tax-free growth and tax-free withdrawals when funds are used for qualified disability expenses. Just as importantly, properly structured ABLE savings generally do not count against means-tested programs such as Supplemental Security Income (SSI) and Medicaid. For individuals who rely on these benefits, saving too much in the wrong type of account can unintentionally jeopardize critical support, making ABLE accounts a valuable planning tool.

How ABLE Accounts Work

The account is owned by the disabled individual, though a parent, guardian, or agent under a power of attorney may assist with management. Contributions are made with after-tax dollars, the account grows tax-free, and withdrawals remain tax-free when used appropriately.

What Counts as a Qualified Disability Expense?

What makes ABLE accounts especially powerful is the broad definition of “qualified disability expenses.” These expenses extend well beyond medical care and can include housing, transportation, education, assistive technology, personal support services, and other costs that support health, independence, and quality of life. For disabled veterans, this flexibility matters. Many service-connected needs don’t fit neatly into traditional benefit categories, yet they are essential to day-to-day stability and dignity.

The Historical Limitation That Affected Veterans

Historically, ABLE accounts came with a significant limitation that excluded many veterans: the disability had to begin before age 26. For servicemembers injured during later enlistments, deployments, or training, or whose conditions developed or were diagnosed years after service, this requirement was a nonstarter.

The 2026 Rule Change: Age Limit Increases to 46

Beginning in 2026, the age-of-onset requirement increases from 26 to 46. This is a substantial and long-overdue shift for veterans. Many service-connected disabilities occur well after age 26, particularly for those who served into their 30s or 40s. Under the new rule, a much larger group of disabled veterans may qualify for an ABLE account for the first time.

Who Qualifies for an ABLE Account?

In addition to the age requirement, the individual must meet the Social Security definition of disability. Veterans automatically qualify if they are already receiving Social Security Disability Insurance (SSDI) or Supplemental Security Income (SSI). Those not receiving these benefits may still qualify through self-certification, attesting under penalty of perjury that they have a medically determinable physical or mental impairment that results in marked and severe functional limitations, has lasted (or is expected to last) at least 12 months or result in death, and began before the applicable age limit.

Why ABLE Accounts Matter for Veterans

For veterans who become newly eligible, an ABLE account can serve as a financial safety valve. It allows savings to exceed the typical $2,000 SSI asset limit without immediately losing benefits, provided balances remain within ABLE-specific thresholds. While SSI cash benefits may be suspended once an ABLE balance exceeds $100,000, Medicaid eligibility typically continues, and overall account limits are often much higher depending on the state. When coordinated thoughtfully, this flexibility can be especially powerful alongside VA disability benefits, which are not means-tested.

Repurposing 529 Education Savings

Another advantage that has become increasingly relevant is the ability, in certain circumstances, to move funds from a traditional 529 college savings plan into an ABLE account. For families who originally saved for education but later faced a disability diagnosis, whether for a veteran or a dependent, this provision allows education savings to be repurposed for disability-related needs without triggering taxes or penalties, subject to annual and lifetime limits.

ABLE Accounts as Part of a Broader Plan

From a planning perspective, ABLE accounts are not a cure-all. They do not replace the need for careful coordination with VA benefits, special needs trusts, or long-term care planning. However, they can complement those strategies by providing accessible, flexible funds for everyday expenses that support independence and quality of life.

A New Opportunity for Disabled Veterans

Now that we are in 2026, ABLE accounts deserve renewed attention, especially for disabled veterans who were previously excluded by outdated eligibility rules. If you or someone you love is a veteran living with a service-connected disability that began later in life, this change may open the door to new planning opportunities. Used thoughtfully, an ABLE account can provide more than tax advantages. It can offer peace of mind, autonomy, and financial breathing room; things every veteran deserves.

Curious about the changes to ABLE and looking for help?  A MFAA financial advisor can help.

 

Categories
Financial Planning Real Estate Taxes

Cost Segregation Studies: A Smart Tax Move… Sometimes

Cost Segregation Studies: A Smart Tax Move… Sometimes

If you are a landlord with rental properties, you’ve probably read an article or listened to a podcast where someone recommended, “Do a cost segregation study to reduce your taxes.” This ‘one-size-fits-all’ approach to tax strategy is nearly always flawed, and cost segregation studies are not an exception to the rule. While you might be able to lower your current tax bill by having a cost segregation study done for your property(s), many landlords – especially the families I deal with most often – will not realize a current benefit equal to the time and expense of the study. 

At PIM Tax Services, we work with hundreds of military and veterans families who own rentals. Many became landlords because a PCS move turned their primary residence into a rental. Others are more intentionally building their long-term wealth through real estate. Regardless of how you came to be a landlord, cost segregation can be a powerful tool, but it’s not an automatic win. This article breaks down what a cost segregation study is, why they are suddenly very popular for small-scale rental property owners, and the biggest reason many landlords won’t see an immediate benefit to their income taxes.

What a Cost Segregation Study Actually Is (in Plain English)

A cost segregation (‘seg’) study is a detailed analysis that separates a building into its component parts, grouping those parts according to their depreciation “lives.”

Normally, a residential rental property is placed into service as one entire unit and depreciated over 27.5 years. That’s the default rule for the building (not the land). A cost seg study recognizes that if parts of the building were replaced (like an interior door or the appliances), the replacement parts would be depreciated over shorter periods than 27.5 years.   It separates the building into its component parts and groups them into categories based on their depreciable life:

  • 5-year property (appliances, carpeting, furniture)
  • 7-year property (security system or window treatments)
  • 15-year property (fences, driveways, and certain landscaping features)

Why does that matter? Because once those components are reclassified into shorter lives, they may qualify for accelerated depreciation, including bonus depreciation and sometimes Section 179. The result can be a much larger depreciation deduction early in the service life of the rental property. Instead of spreading it evenly over 27.5 years, you may recover the costs of purchasing the rental property much faster.

That can be fantastic – if you can actually use the deduction on your tax return. (Not everyone can.)

Why Cost Seg Studies Used to Be Only “For the Big Guys”

Ten years ago, cost segregation studies were usually something you saw with:

  • commercial buildings,
  • large apartment complexes,
  • high-dollar multi-unit investments.

That’s because they were expensive. Traditional cost seg studies often cost thousands of dollars. For a single-family home, it was tough to justify that cost unless the numbers were huge. The amount spent on the cost segregation study often exceeded the amount saved in taxes. The value proposition for paying for the cost seg study just wasn’t there for small-scale rental property owners.

Today, the landscape has changed. There are now newer approaches and providers that can produce a cost seg-style breakdown for a fraction of what they used to cost. That shift is exactly why more landlords are asking about it, and why it might be worth considering even for a single-family home. While they are more affordable than they once were, they still do not provide immediate value for everyone.

Most Small-Scale Landlords Already Have Negative Taxable Rental Income

80%+ of the hundreds of landlords we prepare returns for already have negative cash flow on their rental properties. With mortgage interest, property taxes, insurance, repairs, management fees, travel, standard depreciation, etc., many small landlords end up showing losses on their tax return for their rental property(s). Because our tax code characterizes rents as passive income, losses from rental activity are called “passive activity losses” (PAL).

The issue is whether you’re allowed to deduct those passive activity losses on the current year’s tax return.

Passive Activity Losses (PAL) and Suspended PAL (SPAL)

Under the federal tax code, passive losses are subject to limits. In simple terms:

  • If you have passive losses, you can generally only use them to offset passive income. 
  • If you don’t have enough passive income, those losses often get suspended and carried forward.

When that happens, you end up with Suspended Passive Activity Losses (SPAL) that roll forward year after year until you can use them. You can use them when:

  • the rental unit starts producing passive income (rents collected exceed expenses),
  • you have other sources of passive income to absorb them, or
  • you sell/dispose of the property in a fully taxable transaction 

Your ability to use your PAL/SPAL has a significant impact on the current value of a cost segregation study.

If You’re Already in the SPAL Group, Cost Seg Usually Doesn’t Help Today

If you already can’t use your rental losses because they’re suspended, adding a cost segregation study will not create an immediate tax benefit.

Instead, what it usually does is:

  • increase depreciation deductions,
  • which increases passive losses,
  • which increases the amount of SPAL you carry forward.

Meaning – you may pay for a cost seg study, and your “benefit” is not a reduced tax bill. Instead, you paid for a more rapid increase of SPAL.

That’s not always useless. Suspended losses can absolutely be valuable later, especially in a year when you sell the rental at a gain, or when your passive income increases. But it’s very different from the cost segregation pitch many people hear, which is essentially “instant tax savings.” (And remember, if you took accelerated depreciation expenses and then sell the property, you may be looking at “accelerated depreciation recapture”!)

A Cost Seg Study After the Property Is Already in Service

If you do a cost segregation study in the same year you place a property into service as a rental, the implementation can be straightforward (still technical, but simpler and cleaner).

But many landlords don’t discover cost segregation until the property has been a rental for a few years. If you implement a cost seg study to accelerate depreciation on a property that is already in service, you may need to correct your depreciation expenses for prior years.

That’s where Form 3115 (Application for Change in Accounting Method) applies. A Form 3115 can allow you to “catch up” missed depreciation (or correct depreciation expenses that should have been different) through a Section 481(a) adjustment. If you are changing to an accelerated depreciation schedule, then the Section 481(a) adjustment produces a large (“catch-up”) deduction in the year of change without amending multiple prior-year returns.

Sounds great, right? Yes… except:

  • Form 3115 is complex.
  • It’s not something most DIY software handles well.
  • It’s not something every professional tax preparer is comfortable preparing. 
  • The math for correcting the depreciation expense is also complex. Properties placed in service in 2023 were limited to 80% special bonus depreciation. Properties placed in service in 2024 were limited to 60% special bonus depreciation. This further complicates the calculation of the Section 481(a) adjustment.

And the cost to prepare a Form 3115 can vary widely. If a cost seg study triggers the need for Form 3115, you’re not just paying for the cost seg study, you’re often paying for professional preparation of Form 3115 to implement the study’s findings. In the market, the cost for preparing Form 3115 can range roughly from $250 on the low end to $2,000 or more. A landlord might see a “$400 cost seg study” advertised and think, “That’s affordable.” But the real out-of-pocket cost may be significantly higher once filing requirements are factored in.

That doesn’t mean “don’t do it.” It means know the full cost before you start.

When Cost Seg Can Make Sense for a Small-Scale Landlord

Even with all the caveats, cost segregation can be valuable for smaller landlords in the right situation. Here are a few patterns where it’s more likely to matter:

1) You can actually use the losses

If you’re not limited by passive loss rules, accelerated depreciation can reduce current-year tax. Just ensure you have passive income that allows you to use the additional depreciation expenses a cost segregation study should generate.

2) You have a high-income year and a strategy to match

Some clients (including military members transitioning to civilian jobs or veterans with changing compensation) have income swings such as bonuses, separation payouts, relocation reimbursements, or a big change in W-2 income. A strategy that creates a larger deduction in a specific year might be useful. But only if the passive activity loss rules don’t prevent you from realizing the extra depreciation expenses.

3) You’re planning a sale and want to model the whole lifecycle

Sometimes a cost seg study increases depreciation now, which can increase depreciation recapture later. Depending on your top marginal income tax rate, the net result may still be favorable for you, but don’t assume anything. Run a model to project the tax implications for the unique facts and circumstances of your situation.

4) The property has substantial eligible components

Not all single-family homes are created equally. A basic older home with minimal improvements might not yield much reclassification. A home with significant renovations, extensive land improvements, or higher-cost components may yield more.

The Bottom Line: This Is a Math Problem, Not a Vibe

Here’s the point I want every landlord to take away:

Whether a cost segregation study is valuable is a math problem.

Before paying for a study (even a “cheap” one), you want someone to run the numbers and answer questions like:

  • Will the accelerated depreciation create a deduction I can use this year, or will it just increase SPAL?
  • If I need Form 3115, what will it cost to prepare and file?
  • How long do I plan to keep the property?
  • What’s my expected taxable income trajectory over the next few years?
  • What happens on sale, especially with depreciation recapture and suspended losses?

A cost seg study can be an excellent tool, but it’s not an automatic win for landlords with one or two single-family rentals. For many small-scale landlords, especially those already sitting on suspended passive losses, the “benefit” may be delayed, not immediate.

A Practical Rule of Thumb

If you want a simple way to think about it:

  • If you’re consistently in SPAL territory and don’t expect that to change soon, a cost seg study will usually not produce current year tax savings.
  • If you can use the losses now (or will soon), or you’re modeling a strategic multi-year plan, a cost seg study might be worth it but only working through the math problem will let you know for sure.

Final Thought (and a Quick Disclaimer)

I am a big fan of smart tax strategies, especially the kind that help military and veteran families build wealth without getting surprised at tax time. Cost segregation studies can absolutely be part of that plan. But it’s not a magic button, and the passive loss rules are often the deciding factor.

If you’re considering a cost seg study for a single-family rental, don’t start by buying the study. Start by running the numbers.  If you are wondering where to even start, a MFAA financial advisor can help you decide, connect you with a tax professional, and incorporate your rentals into your overall financial plan.  

Disclaimer: This article is for general informational purposes and is not tax advice. Tax outcomes depend on your full (and unique) facts and circumstances. Always consult a qualified tax professional before implementing a strategy.

Categories
Taxes

Taxes for Teenagers

I knew I was off track when my 21-year-old daughter asked me, “Dad, how much do I get in taxes?” She was either being cheeky, pointing out that I’d failed to teach her about taxes, or both.  Then a week later, she drove it home with a meme picturing a young woman wondering: 

“I don’t get why people think taxes are hard… Step 1: Get your tax forms. Step 2: Give them to your dad.”

This tax season was good for an introspective dad laugh, but it occurs to me that I’m not the first parent who struggled to teach a basic level of tax understanding to his kids. 

If you’ve ever tried teaching your teenager anything that doesn’t come with a dopamine rush, you know the challenge. But like certain other facts of life, you probably don’t want your kid to learn all they know about taxes from things they see on their phone… So,  here’s a short guide for helping your teen understand taxes without over-going their attention span.

Phase 1: Reassurance

The first thing teens should hear is: “You’re not going to jail and we’ll help you.”

Let them know that you’ll help them navigate taxes until they’re ready to handle it themselves. This removes some of the fear because you’ll fly on their wing until they’re ready to solo. 

Phase 2: Taxes For Teenagers 101

Uncle Sam requires us to pay what we owe, no more, no less.  Some adults take a lot of risk trying to min-run their income reporting.  Others run out of time and interest, and they miss legitimate opportunities to suppress their tax bill.  The goal should be to pay just the right amount each month to avoid a big bill or big refund at tax filing time (April 15th). 

In addition to paying what we owe, we need to pay on time throughout the calendar year. Most of the time, our employers help us with this, but it’s ultimately our responsibility to determine and pay the correct amount. There are great free tools, such as calculators at https://www.dinkytown.net/, that can help “pre-game” the tax picture without a PhD in taxes. 

Phase  3: Name That Tax

Teens already know about sales tax from their purchases. But once they start working, they’ll see new taxes come out of their paycheck. Here are the big ones: 

Income Tax: Pays for things like roads, schools, and fighter jets.

FICA Tax: This includes Social Security and Medicare taxes. You might call it a “geezer tax”  because it pays (some) income and (some) medical expenses for the aged. (It also pays these to the poor and disabled.)

Self-Employment Tax: This is really just FICA tax times 2 since you need to pay both the employer share and your own share when you earn money from things like babysitting, lawnmowing and dog walking. 

You don’t need to overwhelm them with all the obscure taxes—like excise taxes or the details of inheritance taxes—but they should understand the ones that show up on their pay stub.

Phase 4: Tax Filing

Taxes tend to be in the background most of the year, then we start to get forms from our employers in January-February. We need to either use a software tool (free to cheap) for DIY’ers, a free service (often available to the military and low-income taxpayers), or a paid professional. 

Generally, taxes need to be filed by 15 April each year. You can always file a simple form to get a 6-month extension, but you’re still supposed pay what you owe by 15 April. “But Dad… how do I know what I owe?”  

Teens and young adults often don’t earn above the standard deduction, so it’s common that they don’t need to file, or they just get a refund of any income tax (not FICA) withholding. 

Phase 5: Don’t Embrace the Refund

Tax refund culture might as well be payday loan and credit-score-worship culture. Each tax season, advertisers glorify all the spending you can do with your tax refund. This teaches our kids that they should give Uncle Sam a negative-interest loan so they can splurge on widgets with a tax refund. 

We’re better off teaching them that while we don’t want to stroke a big check on April 15th, hoping for a refund is mismanagement. Writing Uncle Sam a check (or sending him an ACH… since our kids may not know what checks are) for one dollar is the best-case scenario. 

Cleared to Rejoin

Taxes scare most adults. While our tax situations are often more complicated than taxes for teenagers, our kids need us to teach this fact of life too. As soon as they start earning, it’s time to help them understand their pay stub and file their first return.  Want to find an advisor who could help help you navigate taxes and help with some intro to taxes for your kids?  Check out the MFAA Advisors here. Tax-savvy kids are on their way to being financially healthy adults!

Fight’s On!

Categories
Taxes

The Million Dollar TSP

The Million Dollar TSP

Are you approaching or reached a million dollars in your Thrift Savings Plan (TSP)?  Congratulations!  More than likely, your retirement goal is now funded.  If the entire account is allocated to pretax retirement savings, it’s time to speak with an advisor to do some tax planning.  There are several strategies that can be utilized to reduce the income taxes you will pay over your lifetime.

Meet John and Lisa, an active duty service member and a government employee wanting to retire in their 50’s.  Both are what we like to call super savers; for years they have been maxing out their TSP contributions and their IRA contributions.  In addition, they invested in non-retirement accounts every year.

Roth vs Pretax Contributions

At this point in John and Lisa’s career, their salaries are nearing the career peak.  They are in a higher tax bracket than they were a few years ago and because of that had defaulted to making pretax contributions to the TSP.

We analyzed the income taxes they are paying while working vs projected income taxes in retirement.  Based on that analysis, we determined that pretax contributions were only reducing the annual tax bill by a small amount.  Changing to Roth TSP contributions increases current income taxes modestly but significantly reduces lifetime income taxes.

Retirement Income Plan

Beginning to withdraw 4-6% of the balance in the pretax retirement savings, as soon as they retire, can help to reduce required minimum distributions in the future.  This strategy will not only fund spending needs in retirement but will also reduce their lifetime tax burden.

Roth conversions

For those that want to leave a tax friendly estate to their heirs or are married, beginning to convert some of the pretax retirement savings to Roth can significantly reduce the lifetime tax burden.

Since John and Lisa are married, inheritance of the retirement plan in the event of one spouse’s death must be considered.  Doubling the amount of pretax retirement savings and moving to a higher tax bracket because of the death of the spouse, will significantly increase income taxes for the surviving spouse.  We analyzed how much more income they could realize and stay in the same tax bracket.  We convert this amount each year to a Roth so that the future growth of the assets converted will be income tax free.

Gifts To Charity

Giving back to the community is a priority for Lisa and John.  They make significant charitable gifts each year.  Unfortunately, cash gifts to charity, do not give as much of a tax break as they had in the past.

Lisa and John have some individual stocks that are carrying large capital gains.  We recommended that they gift shares of these stocks to a donor advised fund instead of making cash gifts to the charity.  The charity will still receive their gift, Lisa and John will take the same income tax deduction and as an added benefit, avoid realized capital gains from the sale of their stocks.

Once Lisa and John turn 70, we plan to make the charitable gifts from their pretax retirement accounts.  This will provide a larger tax deduction than making gifts from income or non-retirement savings.  These qualified charitable distributions will also will count towards meeting the required minimum distributions.

Benefits of Tax Planning

These combined strategies have the potential to save over $2,000,000 in lifetime taxes for Lisa and John.  More importantly, it will enable them to retire in their early 50’s and start living the life they have always wanted to live.

If you’re ready to explore how you save on your lifetime income taxes, the MFAA advisors can help.  Find the profiles here.

Categories
Taxes

6 Tax Moves To Consider In 2025

Military Veterans often face changing financial situations, from untaxed benefits and combat zone tax exclusions to special bonuses and, finally, the transition to retirement or a civilian career. As a result, taxes from one year to the next can look drastically different and Veterans should be proactive with their tax planning. Here are six essential tax moves for veterans to consider in 2025.

1. Regularly Update Tax Projections

Tax liabilities can fluctuate based on changes in taxable income, household status, and spouse employment or small business earnings. Staying proactive with tax projections helps avoid surprises and enables strategic financial planning. Many tax moves must be completed during a given calendar year and accurate tax projections are essential information to make decisions. A common mistake for veterans is withholding far too little or far too much from their paycheck for taxes. This can result in overly large tax refunds or tax payments that break the budget at tax filing time.

Why It Matters:

  • Prevents penalties for underpayment of estimated taxes.
  • Identifies if paycheck tax withholding is insufficient.
  • Improves budgeting and cash flow management.
  • Facilitates informed decisions about major expenses or investments.
  • Enables informed decision-making.

Action Step: Develop tax projections for the year and update them whenever you experience major changes in taxable income. I generally develop these tax projections twice per year for clients, once in May and once in November or December`.

2. Switch Pre-Tax TSP Contributions to Roth Contributions if You Earn a Combat Zone Tax Exclusion

If you’re earning a combat zone tax exclusion for part of the year, switching your Thrift Savings Plan (TSP) contributions to Roth can be an effective move. The reduction in taxable income due to the deployment will likely decrease your marginal tax rate for the year, making pre-tax contributions less effective. Contributions made to a Roth TSP while in a combat zone grow tax-free and are withdrawn tax-free in retirement.

Why It Matters:

  • Maximizes the tax-free growth potential of your combat zone income.
  • Ensures you benefit fully from the unique tax advantages of the exclusion.
  • Provides long-term savings flexibility and tax diversification.

Action Step: If you have a scheduled deployment to a combat zone or are in a combat zone, change your TSP contributions to Roth contributions.

3. Switch to Pre-Tax TSP Contributions if You Are Expecting a Retention Bonus

If you’re anticipating a retention bonus in 2025, you may move into a higher tax bracket for the year. Switching to pre-tax contributions in your Thrift Savings Plan (TSP) can help you earn tax deductions at the temporarily higher marginal tax rate.

Why It Matters:

  • Reduces your taxable income in the year you receive the bonus.
  • Maximizes the immediate financial impact of the retention bonus.
  • Gives you the opportunity to convert these contributions to Roth status at a lower tax rate in the future.

Action Step: Login to the TSP website and switch Roth contributions to Pre-tax/traditional. Ensure the pre-tax contributions align with your income projections and overall retirement strategy.

4. Take Advantage of Roth IRA Opportunities

Roth IRAs provide tax-free growth and withdrawals in retirement, making them a valuable option for veterans who meet income eligibility requirements. Additionally, contributions to Roth IRAs can be withdrawn at any time without taxes or penalties. Again, that applies to contributions only. This benefit is unique to Roth IRAs and means that contributions are not “locked up.” Contributions for 2024 can be made until April 2025, offering additional flexibility.

If you are regularly contributing to a traditional IRA, check the rules on the deductibility of those contributions. Often, veterans with access to TSP or another 401K may find that they earn too much income to receive a tax deduction for traditional IRA contributions.

Key Details:

  • Income Limits for 2025: Single filers earning up to $150,000 can make full contributions, with a phase-out up to $165,000. Married filers’ phase-out range is $236,000 to $246,000.
  • Earned Income Requirement: To contribute to a Roth IRA, at least one spouse must have earned income for the year, such as wages, salaries, or self-employment income. This rule allows both spouses to contribute, even if one has no earnings, provided the total earned income meets the contribution limits.
  • 2024 Contribution Deadline: April 15, 2025.
  • 2025 Contribution Deadline: April 15, 2026.

Action Step: Determine your eligibility and contribute to a Roth IRA. If your income exceeds the limits, explore a backdoor Roth IRA contribution. If you need to make a backdoor Roth contribution, work with a financial planner or tax adviser to ensure you don’t run into any tax surprises.

5. Utilize Tax Loss Harvesting

If you have investments in taxable brokerage accounts, tax-loss harvesting can offset capital gains and reduce taxable income.

Why It Matters:

  • Offset capital gains realized during the calendar year.
  • If realized capital losses exceed realized capital gains, you can reduce your other taxable income by up to $3,000 per calendar year.
  • Net losses beyond $3,000 can be carried forward into future years.

Action Step: Review your portfolio before year-end. Identify opportunities to sell underperforming assets while maintaining your long-term investment strategy. Always consider your marginal tax rate as part of this decision. Tax loss harvesting at a low marginal tax rate may be relatively ineffective at reducing your lifetime tax liability.

6. Leverage Tax Gain Harvesting

Veterans with lower incomes in 2025 may qualify for the 0% federal long-term capital gains tax bracket. This means you can sell appreciated assets without incurring federal taxes on the gains, providing a valuable opportunity to reset your cost basis and optimize your portfolio.

How Long-Term Capital Gains Work:

  • Long-term capital gains apply to investments held for more than one year before being sold.
  • For 2025, the 0% tax bracket applies to single filers with taxable income up to $48,350 and married filers with taxable income up to $96,700.
  • Gains beyond these thresholds are taxed at 15% or 20%, depending on your income level.

Why It Matters:

  • Realizes gains tax-free at the federal level for those in the 0% bracket.
  • Resets the cost basis, lowering future tax liabilities.

Special Opportunity for Veterans: This strategy is particularly beneficial for veterans who deploy to a combat zone during the year. Combat zone tax exclusions often lower taxable income significantly, making it easier to qualify for the 0% long-term capital gains bracket.

Action Step: Complete your tax projections before the end of the calendar year to determine if you will fall into the 0% bracket. If you do, sell assets at a gain without crossing into the 15% tax bracket.

Note that this strategy applies to federal taxes and is most beneficial for veterans who have tax residency in a state without income taxes or do not tax any income earned by active duty service members. Most states with income taxes also tax capital gains.

Final Thoughts

For military veterans, proactive tax planning is an essential part of building a secure financial future. Implementing these strategies in 2025 can help reduce your tax burden either in 2025 or over the course of your life.

The critical step in each case is to develop tax projections to facilitate these tax moves.  MFAA members are financial planners who works with military and veterans and can help with your tax moves and many other financial planning issues.  Click here to get started.

 

Categories
Taxes

Tax Tips and Understanding the New 1099-K Reporting Requirements

Note: This post provides information accurate as of the date of publication and is provided for educational purposes. For personalized advice, consult with your own tax advisor.

Tax Planning Tips

Tax planning is crucial for small business owners, individuals making money selling things online and anyone earning income from a side hustle. The profit from these activities is considered taxable income and there are steps that you can take now to ensure a smooth tax season. Here are a few tips to get you started:

  1. Start tracking your income and expenses – Utilize software programs or spreadsheets to help you stay organized.
  2. Make quarterly tax payments – Quarterly payments, also known as estimated tax payments, are payments made by individuals or businesses to the Internal Revenue Service (IRS) on a quarterly basis to cover their tax liabilities. These payments are typically required when taxpayers do not have taxes withheld from their income through regular paycheck withholdings. Every state has different requirements so check your individual state to determine if you need to make payments to your state.
  3. Track your mileage – Use an app or a good old-fashioned notebook to track your miles for work. Not sure if this applies to you? The IRS provides guidelines on who can deduct mileage or vehicle expenses for work here.
  4. Open a retirement plan – Consider options like a SEP IRA or Individual 401(k) to reduce your tax burden and save for the future! Need help? Reach out to one of our MFAA advisors to help you put a plan in place.

Lastly, if you’re self-employed or have income from a side hustle, you may receive various forms such as 1099-NEC, 1099-MISC, and 1099-K. The remainder of this blog will focus on Form 1099-K and the upcoming changes implemented by the IRS.

Decoding Form 1099-K

The reporting threshold for third-party settlement organizations, which include payment apps (e.g., Zelle, Venmo, CashApp) and online marketplaces (e.g., eBay, Etsy, Facebook Marketplace), was changed to $600 by the American Rescue Plan Act of 2021. This act mandated that all third-party settlement organizations report payments of more than $600 for the sale of goods and services on a Form 1099-K starting in 2022. These forms would be submitted to the Internal Revenue Service (IRS) and provided to taxpayers to assist them in completing their tax returns. Prior to the American Rescue Plan, the reporting requirement applied only to the sale of goods and services involving more than 200 transactions per year, totaling over $20,000.

The implementation of this requirement has been delayed but the IRS has taken steps in 2023 and 2024 to begin phasing in this threshold (currently $5,000 for 2024).

Now that you are thoroughly asleep, let’s dive into how this might apply to you. 

What’s Taxable?

Any profit from the activities described above would be considered taxable income. For instance, if you bought a Tickle Me Elmo at the start of 1996 for $30 and sold it for $1,500 in December, the difference would be considered taxable income. However, if you sold it for $25, there would be no taxable income.

What’s NOT Taxable?

According to the IRS, “You shouldn’t receive a Form 1099-K for personal payments, including money received as a gift and for repayment of shared expenses.” This money wouldn’t be considered taxable, but that doesn’t mean you won’t accidentally receive a 1099-K! Good recordkeeping will prevent any frustration during tax season. Ensure you mark those payments as personal on third-party systems whenever possible.

Help! I Received a 1099-K and I Shouldn’t Have

Unfortunately, neither the IRS nor your tax preparer can correct your incorrect 1099-K. You’ll need to contact the issuer to rectify the error. They will need to issue you a 1099-K with a zero amount.

I Received a 1099-K But It’s Wrong

Your best course of action is to have the issuer send you a correct form. This is also not something the IRS or your tax preparer can do for you. To quote our favorite agency, “Don’t contact the IRS. We can’t correct your Form 1099-K.”

Keep in mind that tax laws and regulations may change over time. For personalized advice tailored to your specific circumstances, it’s always wise to consult with a qualified tax advisor.  Many of the MFAA advisors are tax planning experts, you can find them here..

Categories
Taxes

When Veteran Business Owners Should Make an S Corp Election

Many military members and Veterans are venturing into business ownership these days. In fact, 5.5% of business owners in the U.S. were Veterans in 2024. With business ownership comes a host of important and complex decisions. One of which is what entity type to select.

Most businesses start as Limited Liability Companies (LLCs). As the business grows in employee headcount and revenue, it is important to re-assess your entity structure to ensure that it aligns with your personal and business goals. One of those decisions that a successful LLC owner may come up against is the decision to make an S Corporation (or “S Corp”) election.

The goal of this article is to demystify S Corp elections and empower business owners to make informed decisions about the direction of their business.

Why Should You Care About S Corp Elections?

The main reason behind making an S Corporation election is to lower your tax bill. Specifically, we are talking about self-employment taxes. The self employment taxes consist of a 12.4% social security tax up to the first $176,100 in profit in 2025 and a 2.9% Medicare tax on all income. This amounts to a 15.3% tax on the first $176,100 in profit. These profits are also subject to Federal and State tax, so the total tax bill can add up quickly.

Many business owners are confused about exactly when it makes the most sense to elect S Corporation status. Choosing the right time to make this election can save or cost thousands or tens of thousands of income tax.

What Is an S Corp Election?

An S Corp election is a tax status that lets your business profits flow directly to your personal tax return, avoiding double taxation. To be eligible for an S Corporation, you must be U.S. based, have fewer than 100 shareholders, and have a single class of stock.

How this works is you pay yourself a reasonable salary on payroll, and then the excess profit flows to your return to be taxed at Federal and State levels, bypassing any self employment taxes.

For example, if a business owner has a profit of $100,000, the self employment tax on a simple single member LLC will be $15,300. However, if that business owner elects S Corporation status and pays themselves a reasonable salary of $50,000, the self employment taxes will be $7,650, which would save the business owner $7,650 in tax.

Who Should Consider an S Corp Election?

An S Corporation election is going to be most beneficial for small business owners that make a significant profit, usually defined as $50,000 to $100,000 and higher. It is not going to be best for those who have a side gig that may make profit one year and not the next, or for those with more complex ownership structures that require several different classes of stock and might be better suited by a C Corporation.

How to Make an S Corp Election

Here are the steps to file an S Corporation Election:

  1. File IRS Form 2553 by March 15 or within 75 days of forming your business.

 

  1. Set up payroll to pay yourself a reasonable salary. The definition of “reasonable salary” is not well defined by the IRS but should be reasonable if you were to get audited.

 

  1. Update your bookkeeping, tax, and payroll practices. This includes keeping tight bookkeeping in a software like QuickBooks, filing an S Corporation return, and running payroll. This will all increase your administrative costs from a few hundred to few thousand dollars per year.

With these changes, you can expect more administrative burden, cost, and compliance concerns around paying yourself a reasonable salary. The S Corporation structure is certainly more complex than a simple Sole Proprietor, but the payoff can be well worth it in the right situation.

How Will This Benefit Your Business?

The primary benefit of making an S Corporation Election is lower self employment, otherwise known as payroll taxes. As discussed at the top of the article, this happens by lowering the amount of income coming to you in wages which is double taxed by both halves of the 6.2% Social Security tax and 1.45% Medicare tax for a total tax’s of 15.3% on the wage base of $176,100 in 2025. So instead of your entire pay being subject to payroll taxes, only the amount paid to you as a reasonable salary will be taxed at that 15.3% rate. The rest will come to you as an owner’s distribution to be taxed solely at your federal and state income tax rates.

Common Mistakes and How to Avoid Them

Making an S Corporation election is not without risk and mistakes, but with some planning and foresight you should be able to avoid these. The main mistake would be paying yourself an unreasonably low salary, thereby minimizing the percentage of your income that is subject to Social Security and Medicare taxes. If the IRS finds this in an audit and can be extremely costly in penalties.

Another mistake would be choosing S Corp status before your business is consistently profitable. If your business turns extraordinarily little in profit or even loses money, you will not be able to reap the benefits of taking owner’s distributions as your entire profit will go to paying your salary or paying business expenses. This results in you unnecessarily paying hundreds to thousands of dollars in payroll, tax preparation, and compliance costs.

Avoiding these mistakes is completely attainable. Here are three simple steps you can take:

  1. Consult a financial advisor and/or trusted tax preparer.
  2. Use professional payroll software to handle compliance.
  3. Get a reasonable compensation study completed.

Conclusion

Making an S Corporation election can be extremely beneficial for military and veteran business owners. The main benefit is saving on payroll taxes by paying yourself a reasonable salary and then taking the rest as an owner’s distribution. You have to be careful to set a reasonable salary, setup a proper payroll system, and hire a tax preparer to file your S Corporation business return.

Ready to explore whether an S Corp election is right for you? Contact a trusted Military Financial Advisor’s Association member to map out a tax-saving plan that fits your business and personal goals.

 

Categories
Taxes

Military Tax Preparation Options

In addition to being an investment advisor, I am also a tax professional. People will sometimes jokingly accuse me of preferring complicated tax laws because complicated tax laws help my tax business grow. If ordinary citizens struggle to prepare their own tax returns, they are more likely to pay me to do it for them. I understand their logic, but it doesn’t apply to me. I don’t like complicated tax laws. I am appalled that our Congress has created a tax system so complicated most Americans don’t understand it and will penalize us if we fail to comply with it. I am waiting for a class action lawsuit about this, and I will jump on it with both feet!

Fortunately, most military families do not have a terribly complicated federal tax return. With the broad array of free (or low cost) resources available most military families can get their tax returns reliably prepared and filed each year without consulting a tax professional. There are some exceptions, of course. Some military families have complicated financial lives and their tax returns become more complicated as a result. More often than not, however, military families can use one of the free software options available, step through the questions the software program asks, and get the correct result. I encourage military families to explore this option for their tax preparation. Not only is it free, but I think self- preparing your tax return helps you understand your financial situation a little better.

There is one trap on the self-preparation trail that I want you to know about and avoid, though. The software is not a panacea. It does not know everything, and it will allow you to prepare and file an incorrect return. Do not believe that just because your tax prep software allowed you to claim certain deductions or credits that you have reasonable authority to do so. The tax software often does not know that you have entered incorrect information. The software company takes no responsibility for your incorrect return if you entered incorrect information. Likewise, the IRS will hold you responsible for the return. They do not accept, “My software let me do it, so I thought it was correct” as an excuse.

The US Tax Court recently reaffirmed this position when they issued TC Summary Opinion 2024-15 in the case of Pope vs Commissioner of Internal Revenue. The Popes self-prepared and filed their 2020 tax return using tax preparation software. On their 2020 tax return the Popes claimed a $14,000 adjustment on Schedule 1 for IRA contributions. This was done in error. The contributions were to Mr. Pope’s 401(k) retirement plan through his employer, and not to an IRA. The contributions to the employer-sponsored plan should not have been recorded as an adjustment on Schedule 1. The IRS recognized this error, disallowed the adjustment, and charged the Popes additional taxes and interest.

The Popes challenged the IRS decision in Tax Court. At trial Mrs. Pope testified that she entered the amount of the 401(k) contribution believing the tax preparation software would alert her if it was incorrect. Unfortunately, tax prep software does not work like that. User errors will often go unchecked. In the Pope’s case, the amount entered exceeded the legal limit for 2020 contributions to an IRA, yet the software did not alert the user. In the Summary Opinion, the Tax Court pointed out the IRS publishes instructions for form 1040 each year, and taxpayers are advised to consult those instructions even if they are using tax preparation software. The Tax Court ruled in favor of the IRS, and the Popes were required to pay the additional tax plus interest.

Do not avoid self-preparing your tax return just because things went poorly for the Popes but learn from their mistakes. If you feel confident you can prepare an accurate tax return, then you can definitely save time and money doing it yourself. If you are not sure about a question you are being asked by the software, don’t guess. Get clarification from the software company for the brand you are using or look it up yourself. You can usually find the answer using the current year instructions for form 1040. They are found online (IRS.gov) and give line by line instructions for filling out that form. Avoid relying on sources that are not authoritative. Thousands of bloggers and social media gurus are offering free tax advice. Much of it is inaccurate and even more of it is outdated and no longer applicable. Ony use sources that would hold up in court if you had to tell a judge where you got the information that you relied upon to prepare your tax return!

If you have a complicated situation, you might consider hiring a tax professional to prepare your return for you. If you are searching for a tax professional who understands military tax issues, check out the Military Tax Experts Alliance. You can submit a question or find a tax professional to work with. It’s a great organization, and I just happen to be a member!

No matter how you get your taxes prepared, just remember to get them submitted on time. The IRS is not very friendly to late filers!

If you’ve got financial questions that are (or aren’t) tax-related, the MFAA financial planners are a great source of help.