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Feature: Kicking Yourself for Not Doing More 2025 Tax Planning? (4 min)
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SMB NEWS: Florida Property Tax Relief: Not for SMBs (here is a short and sweet summary)
Florida lawmakers are pitching HJR 203 as “property tax relief,” but it is really a targeted break for one group: people who live in their own Florida homes full-time. The measure, which has passed the House and is now waiting on the Senate, would eliminate the non-school portion of property taxes charged by cities, counties, and most local districts on homesteaded primary residences starting in 2027, but only if it is placed on the November 2026 ballot and at least 60% of voters approve it.
The school portion of the tax bill would not change, so the typical homeowner would still owe roughly 40% of today’s bill, with the exact share varying by county.
Commercial property, rental housing, and non-homestead second homes get no relief and continue under the current rules. Local governments would lose a large share of revenue from owner-occupied homes while still being expected to fund core services such as police and fire, which is likely to mean more pressure on the remaining tax base — especially businesses and landlords — or cuts in other services that businesses rely on.
Kicking Yourself for Not Doing More 2025 Tax Planning?
If you are staring at your 2025 income numbers thinking, “I should have planned better,” you are not alone. Many business owners discover their tax problem only after the year is closed.
December 31 shuts some doors. It does not shut all of them.
A handful of meaningful moves remain available before you file. Most involve prior-year contributions and careful reporting. None are exotic. All are practical.
1. Contributions That Still Count for 2025
Traditional and Roth IRAs
If you qualify, you can still make a 2025 IRA contribution up to the regular April filing deadline and designate it for 2025.
Important: a filing extension gives you more time to file your return, not more time to fund an IRA for the prior year. The contribution deadline is generally the unextended due date.
If you are eligible for a deductible traditional IRA contribution, the deduction reduces your 2025 taxable income. If you are funding a Roth, there is no current deduction, but the contribution still counts toward your 2025 limit.
Before you fund it, confirm income phaseouts and workplace plan rules. A contribution only helps if it is allowed and properly reported.
Health Savings Accounts (HSAs)
If you were covered by a qualifying high-deductible health plan in 2025, you can generally make a 2025 HSA contribution up to the unextended due date of your 2025 return.
Two practical points:
Tell the HSA custodian the contribution is for 2025.
Make sure you were actually HSA-eligible during the months you are claiming.
HSAs remain one of the most efficient tools in the Code: deductible going in, tax-deferred growth, tax-free withdrawals for qualified medical expenses. If you missed funding it during the year, this is one of the few clean second chances.
Self-Employed Retirement Contributions (SEP IRA)
If you are self-employed, your lever may be larger.
For many sole proprietors and single-member LLC owners, a SEP IRA allows an employer contribution for 2025 to be made up to the due date of the business return, including extensions.
That extension point matters. Unlike IRA contributions, SEP contributions can generally follow a properly filed extension.
The calculation is income-based and mechanical. It is not something to guess at - talk to your CPA. But if your 2025 income was strong, this can materially reduce taxable income.
2. Use the Return as a Planning Tool
Even when the year is closed, reporting choices can change the final number.
Standard Deduction vs. Itemizing
In 2025, the deduction for state and local income and property taxes is capped (generally $40,000, or $20,000 if married filing separately). If you are considering itemizing because of high property taxes, run the math using the cap.
Mortgage interest, charitable contributions, and medical expenses may push you over the standard deduction. But medical expenses help only to the extent they exceed the percentage-of-AGI threshold. Confirm you clear that hurdle before assuming they matter.
Run the return both ways.
Your Filing Status
That small box controls brackets, phaseouts, and credit eligibility.
If you were newly married or divorced in 2025, or if you supported dependents in a way that might qualify you for head-of-household status, confirm the rules rather than guessing. The correct status can shift the result meaningfully.
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3. If You Cannot Change the Tax, Change the Penalty
Sometimes the tax itself is largely fixed. The penalty may not be.
Underpayment Safe Harbors
Many taxpayers avoid the underpayment penalty if they:
Owe less than $1,000 after withholding and credits, or
Paid at least 90% of their 2025 tax, or
Paid 100% of their 2024 tax (higher-income taxpayers may need to pay 110%).
If your income was uneven during the year, the IRS allows an annualized income method (Form 2210, Schedule AI) that can better match payments to when income was earned.
In cases involving disaster, casualty, or unusual circumstances, the IRS has authority to waive penalties when it would be inequitable to impose them.
The tax may be fixed. The penalty calculation often is not.
Installment Agreements
If you cannot pay in full, an installment agreement can prevent escalation with the IRS.
Interest and applicable penalties generally continue until the balance is paid. But structured payment is better than ignoring the bill - talk to your CPA if you need time to pay.
4. Make 2026 Boring
The most valuable move you make this spring may not affect 2025 at all.
Once your 2025 return is complete:
Adjust 2026 withholding or estimated payments to prevent the problems that you encountered in 2025.
Put calendar reminders mid-year and early fall to review profits, gains, and contributions.
Keep a short checklist of what nearly went wrong this year: retirement contributions, HSA eligibility, charitable acknowledgments, cost basis verification.
Tax planning works best when it is dull and timely.
You cannot rewrite 2025. You can prevent it from repeating. The goal is not brilliance, it is steadiness.
And steadiness, unlike December 31, does not expire.
Editor’s note: The above is general business advice. You should consult your CPA sooner rather than later - especially if you are concerned about your 2025 tax liability.
Have an interesting business question and need a free bit of advice? Send your question to [email protected]. No confidential info, please!



