#tax-planning
Strategic tax planning to minimize liability and maximize savings
A 35-year-old is six times more likely to become disabled than to die before 65, yet most buy-sell agreements only plan for death. How disability buy-out (DBO) insurance funds a co-owner buyout — elimination periods, cross-purchase vs. entity redemption, and why premiums are nondeductible but proceeds are tax-free.
Starting January 1, 2026, OBBBA's new IRC §274(o) cuts the employer deduction for on-site cafeterias, office snacks, and "convenience of the employer" meals from 50% (or 100%) to zero, while client meals, travel meals, and restaurant employee meals keep their old treatment. Here's the math on what the change costs and how small businesses should restructure their books.
The Educational Choice for Children Act creates a $1,700 federal income tax credit for cash donations to K-12 Scholarship Granting Organizations, starting with the 2027 tax year — but only in states that opt in. Here is how the nonrefundable, cash-only Section 25F credit works, the five-year carryforward, the 90% pass-through rule for SGOs, and why pass-through business owners should track their state's participation through 2026.
Starting tax year 2026, the OBBBA limits gambling loss deductions to 90% of winnings. Breakeven gamblers may owe IRS tax on phantom income from the 10% gap.
Esports organizations must separate prize revenue from player distributions, recognize sponsorship revenue under ASC 606 as obligations are delivered, and track the 2026 rise of the Form 1099-NEC/MISC filing threshold from $600 to $2,000 per payee.
For 2026 the IRS caps total 401(k) contributions at $72,000 versus a $24,500 employee deferral limit; business owners can convert the after-tax gap between the two into a Roth account tax-free using the mega backdoor Roth strategy.
Boatsetter and GetMyBoat report gross transaction volume on Form 1099-K, not your net payout, so record the full charter price as revenue and the platform commission as a separate expense — and track bareboat versus captained bookings separately, since adding a captain shifts income from Schedule E to Schedule C self-employment tax.
A $150,000 CNC lathe bought at auction and fully expensed under 100% bonus depreciation can generate roughly $37,500 in first-year tax savings at a 25% effective tax rate, but only if the buyer's premium, sales/use tax, and rigging costs are correctly capitalized into cost basis first.
Solar ground leases on farmland pay $500-$1,200 per acre annually nationally once construction begins, but landowners who skip the decommissioning bond, rollback-tax reimbursement, and escalator clause often lose more than they gain over a 20-to-35-year term.
Starting with tax year 2026, employers must separately report qualified overtime compensation on Form W-2 using Box 12, Code TT — but only the FLSA-required premium half of overtime pay qualifies, capped at $12,500 for single filers and $25,000 for joint filers.
Authors receiving publisher AI-licensing checks — including payouts from Anthropic's roughly $1.5 billion author settlement — should verify their contract grants those rights, confirm they're getting the Authors Guild-recommended 75-85% split, and report the income on Schedule C as self-employment income, not Schedule E.
Locum tenens and travel-healthcare clinicians are 1099 contractors who owe 15.3% self-employment tax, must establish a valid IRS tax home to deduct travel costs, and often file non-resident state returns for every state where they worked.
