Weekly writing on the planning conversations that move the needle: S-Corp elections, equity compensation, real estate, and the IRS rules behind them.
Selling on the vest date costs almost nothing in tax, and the proceeds are the only funded source for the April bill the 22% withholding rate leaves behind. Here is what waiting a year for long-term rates is actually worth in 2026 dollars, and the two times I tell someone to wait.
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A cabin closed in November, cost-segregated, and listed by December can put a six-figure loss against 2026 wages. It only works if the property, the guests, and your hours all fit inside the weeks that are left, and one family Christmas there can cost $17,289.
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Over the life of the vehicle, a lease and a purchase deduct the same thing: the business share of what the vehicle actually cost you. The 2026 decision is about timing, and on a truck rated over 6,000 pounds the timing is worth $64,132 in one year.
Read postThe regulation does not require a contemporaneous log, which is the opposite of what you have been told. What it requires is hours that actually happened, and in 2025 the Tax Court threw out 744 of one owner's claimed hours because being on call is not working.
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Unvested units are forfeited on the termination date your equity plan reads, and that date is the one number in a separation agreement still open to negotiation. Eight days decided a 1,250-unit tranche worth $59,000, or $34,338 after federal, Medicare, and Utah tax.
Read postFor 2026 the business mileage rate is two rates: 72.5 cents a mile through June 30 and 76 cents from July 1. The bigger decision is which method you start with, because claiming bonus depreciation on the car in year one closes the mileage door for as long as you own it.
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A $4,000 study on a $450,000 rental really does produce a $69,928 first-year deduction. For a W-2 household with one long-term rental, that deduction is worth exactly $0 in 2026, and the same study on the same house saves $17,160 for the owner next door.
Read postYour broker is required to report the strike price alone as your cost basis, which turns a same-day exercise that made nothing into a $200,000 capital gain. Here is the 2026 math and the one line on Form 8949 that fixes it.
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The 60/40 rule is not in the tax code, and on $800,000 of profit it costs $26,337 more than the salary that actually minimizes 2026 federal tax.
Read postRenting out your old house keeps the $500,000 home sale exclusion alive for exactly three more years, and the nonqualified use rule everyone warns you about does not apply to you. Close the sale one day late and a $9,789 tax bill becomes $71,378.
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A partnership that extends its own return can send your K-1 as late as September 15, 2027. File Form 4868, but send an April payment built from last year's K-1, because the extension does nothing for the tax itself.
Read postAn acquisition turns years of unsettled RSUs into a single year of W-2 wages, and payroll withholds the 22% supplemental flat rate on all of it. On a $286,000 payout the real federal income tax is $97,050, so $34,130 shows up as a balance due nine months later.
Read postActive participation gets you up to $25,000 of rental losses against W-2 income, but the allowance falls by $1 for every $2 of modified AGI over $100,000 and reaches zero at $150,000. A $14,000 December bonus can cost $4,300 in federal tax because of what it does to that allowance.
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