Year-End Tax Planning if You're Selling Your Business in Southwest Florida

We got two calls this week that circled the same question from different directions. One was a Fort Myers business owner asking whether closing in December instead of January actually makes a difference. The other was his CPA, asking whether the tax law changes from last year affect how the sale should be structured. Both are good questions, and both are timely. We are into the fourth quarter now, and a deal that wants to close before December 31 needs to be well underway today, not starting in November.

Here is what actually changed in the tax code this year, what a normal Southwest Florida business sale gets from it, and what the calendar itself requires regardless of what the tax code says.

What Changed in the Tax Law This Year

Congress made two permanent changes in 2025 that carry straight into how a 2026 sale gets taxed, and both work in a seller's favor.

The first is bonus depreciation. One hundred percent first-year bonus depreciation is back, permanently, for qualifying property placed in service after January 19, 2025. On an asset sale, this mostly benefits the buyer, who can write off equipment, vehicles and other depreciable assets in the first year instead of spreading it over five or seven. That matters to you as a seller because a buyer who gets a larger first-year deduction can often justify paying more for the assets, and it is worth raising in negotiations rather than leaving it for the buyer's accountant to point out later.

The second is the qualified business income deduction. The 20 percent QBI deduction, which was set to expire at the end of 2025, is now permanent. If you operate as an LLC or S corporation, which describes most of the businesses we sell here, that deduction can apply to income you report in the year of the sale, not only to a buyer's future earnings. It is worth a specific conversation with your CPA about how much of your 2026 income, including any gain that passes through as ordinary income, that deduction can shelter.

There has also been a lot written this year about a more generous exclusion for qualified small business stock, often called QSBS. We want to be straight with you about it: that provision applies to actual stock in a C corporation, held a minimum of three years, and it almost never comes up in the deals we handle. Most businesses that trade in Naples, Fort Myers, Cape Coral and Bonita Springs are LLCs or S corporations sold through an asset sale, not a C corp stock sale. If your CPA raises QSBS with you, ask directly whether your entity even qualifies before it changes any part of your plan.

The Installment Sale Still Does the Heaviest Lifting

None of the changes above touch the tool that actually moves the needle for most sellers we work with: spreading the sale across more than one tax year through an installment sale. When part of your proceeds come in through a seller note rather than all cash at closing, you generally recognize the gain as you collect it, reported each year on Form 6252, instead of all at once.

We already see this often, because seller financing is common in deals here. We wrote about the mechanics of that in more detail this summer, and the link is below. The tax treatment is a second reason to consider it, beyond bridging a financing gap between your price and what the buyer's bank will lend. A gain of $1.5 million taxed entirely in one year can push you into a materially higher bracket than the same gain collected across three or four years of note payments. Your CPA can run the actual numbers against your other income, but it is worth asking the question before you agree to deal terms, not after the papers are signed.

Why the Calendar Matters as Much as the Tax Code

Even with a favorable tax picture this year, closing a deal has its own timeline, and that timeline does not care what the tax code says. An SBA-financed acquisition typically runs 60 to 120 days from a signed letter of intent to the closing table once you account for the buyer's financing, the lender's underwriting, and due diligence on both sides. Count backward from December 31 and the math gets uncomfortable fast if you have not already found a buyer.

That is not a reason to rush a deal that is not ready. It is a reason to have your financials, your add backs, and your documentation in order now, so that when the right buyer shows up, you are not the one holding up the calendar. We would rather see a seller close clean in February with fully prepared numbers than force a December closing that skipped diligence steps just to hit a date.

A Short Checklist Before December 31

• Ask your CPA to model your actual gain under an all-cash close versus an installment sale, using your real numbers, not a rule of thumb.
• If you already have a deal in motion, confirm with your lender's team whether a December closing is realistic given where diligence stands today.
• Pull your 2024, 2025 and year-to-date 2026 financials and get them clean and organized. Buyers move faster on complete records, and every week lost to disorganized books is a week closer to missing the year.
• If bonus depreciation applies to recent equipment purchases, make sure your CPA has that documented before a buyer's accountant asks about it during diligence, not after.
• Talk to your CPA before you talk to a buyer about price. Knowing your after-tax number changes what you are actually willing to accept.

What We Would Do Right Now

If selling before year end is genuinely on the table, three things are worth doing in the next two weeks. Get your CPA the actual deal structure you are considering, cash versus a seller note, so they can run real numbers instead of estimates. Get your financials current through the most recent month, because every buyer's lender will ask for them and stale numbers cost you time you do not have. And have an honest conversation with your broker about whether the market for your specific type of business supports a realistic closing date this year, because not every business should force a December close just to catch this year's tax picture.

After nearly a decade doing this in Southwest Florida, the sellers who come out ahead are rarely the ones chasing a deadline. They are the ones who got their numbers and their tax position sorted out early enough that timing became a choice instead of a scramble.

This article reflects tax law and program information as of September 28, 2026. Tax laws change, and every seller's situation is different depending on entity type, prior depreciation taken, state residency and total household income. This is not legal, tax or investment advice. Consult your own CPA and attorney before making decisions about the timing or structure of a sale.