470 tagged with "Tax Planning"
Strategic tax planning to minimize liability and maximize savings
ISO AMT in 2026: Bargain Element, Form 6251 Line 2i, and the OBBBA Phase-Out Cliff
Under OBBBA, the 2026 AMT exemption phases out at $500K single / $1M joint with a 50-cent rate, doubling the stealth bracket on ISO exercises. Here is exactly how the bargain element flows into Form 6251 line 2i, when a same-year disqualifying disposition eliminates the AMT adjustment, and how to plan exercises to avoid a six-figure phantom-income tax bill.
Qualified Charitable Distributions in 2026: A $111,000 Tax-Free Path From IRA to Charity
A complete 2026 guide to Qualified Charitable Distributions — the IRS-sanctioned strategy that lets retirees age 70½ and older route up to $111,000 from an IRA directly to a qualified charity without recognizing the distribution as taxable income.
S-Corp Basis, Form 7203, and the Phantom Distribution Trap: A Section 1366(d) Guide
Section 1366(d) caps S-corporation loss deductions at stock basis plus direct shareholder debt, and Form 7203 is how the IRS verifies the math. A working guide to suspended losses, phantom capital gains on distributions, the $25,000 open-account debt rule, why personal guarantees do not create basis, and how the Regulation 1.1367-1 ordering rules decide which losses survive each year.
Section 1061 Carried Interest Three-Year Holding Period: How Hedge, PE, and VC Fund Managers Lose Long-Term Capital Gains Without It
Section 1061 recharacterizes carried interest gains from long-term to short-term unless the underlying asset was held more than three years — a 17-point federal rate swing for hedge, PE, and VC fund managers. A practitioner guide to applicable partnership interests, Worksheet A and B reporting, the capital interest exception, and 2026 planning moves.
Section 1212 Capital Loss Carryover: The $3,000 Annual Cap, Indefinite Carryforward, and Why Character Survives Across Tax Years
A practical guide to IRS Section 1212 for individual investors: the $3,000 annual ordinary-income cap, indefinite carryforward, short-term vs. long-term character preservation, the Schedule D ordering rules, and how wash sales interact with carryovers.
Section 1244 Small Business Stock: How Founders Convert a Failed Startup Into a $50,000 Ordinary Loss
Section 1244 lets eligible founders and early investors convert up to $50,000 ($100,000 joint) of capital loss on failed C-corporation stock into ordinary loss deductible against W-2 wages, freelance income, or interest. This guide covers who qualifies, the $1 million capital ceiling, Form 4797 reporting, and the formation steps that keep the deduction defensible.
Section 1245 vs. Section 1250: How Depreciation Recapture Erodes Your Bonus Depreciation Benefits
When you sell depreciated business property, Section 1245 recaptures prior depreciation as ordinary income (up to 37%), while Section 1250 caps the recapture on real estate at 25% — turning a 100% bonus depreciation deduction into a large tax bill at exit unless you plan with cost segregation, 1031 exchanges, and a clean fixed-asset register.
Section 1259 Constructive Sales: How Hedging Appreciated Stock Can Trigger a Phantom Tax Bill
Section 1259 treats short-against-the-box trades, equity swaps, and tight collars on appreciated stock as constructive sales — taxable today, even with no proceeds. Covers the variable prepaid forward workaround, the 30-day closing exception, and the related-party trap.
The Self-Employed Health Insurance Deduction: How Section 162(l) Beats Itemizing
Section 162(l) lets sole proprietors, partners, and more-than-2% S-corp shareholders deduct health, dental, vision, LTC, and Medicare premiums above the line on Schedule 1, line 17 — bypassing the 7.5%-of-AGI floor that gates itemized medical deductions. Form 7206 enforces three limits — earned income, subsidized-coverage months, and PTC coordination — and S-corp owners must include premiums in W-2 Box 1 (not Box 3 or 5) to preserve the deduction.
Section 179 vs. 100% Bonus Depreciation Under OBBBA: How Small Businesses Should Choose Equipment Write-Offs in 2026
OBBBA permanently restored 100% bonus depreciation and raised the Section 179 cap to $2.56M for 2026. A practical framework for small businesses to choose between them — covering taxable-income limits, state decoupling, SUV caps, and the new Section 168(n) qualified production property deduction.
Section 197 Intangibles: 15-Year Amortization for Goodwill, Customer Lists, and Non-Competes
Section 197 requires buyers in a taxable asset acquisition to amortize acquired intangibles — goodwill, customer lists, workforce in place, covenants not to compete — straight-line over 180 months. This guide walks through Form 8594 purchase price allocation, the anti-churning rules for related-party deals, the no-loss rule on dispositions, and Form 4562 reporting across the full 15-year cycle.
Section 199A SSTB Limitation: Why High-Earning Doctors, Lawyers, and Consultants Lose the 20% QBI Deduction
Section 199A's 20% QBI deduction phases out entirely for high-income doctors, lawyers, consultants, and other specified service trades or businesses (SSTBs) — costing a married surgeon at $700,000 of K-1 income roughly $52,000 a year. This guide covers the 2026 income thresholds (~$394,600 MFJ phase-in, ~$544,600 fully phased out), the de minimis safe harbor at 10% / 5% of receipts, the anti-"crack and pack" rules under Reg. §1.199A-5(c)(2), and practical strategies like defined-benefit plans and W-2 wage planning to preserve the deduction.