#tax-deductions
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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 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 170(h) lets landowners deduct the value lost when they place a permanent conservation restriction on real property, but the IRS has labeled high-ratio syndicated structures listed transactions and now disallows over 90% of the claimed deduction in court. This guide explains the four-part qualification test, the 2.5x basis cap under Section 170(h)(7), the 40% strict liability penalty, Form 8283 requirements, the six-year statute of limitations, and the 2026 IRS settlement window.
Section 170(h) lets landowners deduct the diminution in fair market value caused by a perpetual conservation easement, but syndicated versions now face a 2.5x partnership-basis cap under SECURE 2.0, a 40% gross valuation misstatement penalty, and an average 6% Tax Court allowance rate at trial.
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 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'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.
Section 199A's SSTB rule denies the 20 percent qualified business income deduction to high-earning doctors, lawyers, consultants, and financial advisors. In 2026 the joint-filer phase-out runs from $403,500 to $553,500, and OBBBA added a permanent $400 minimum deduction for active business owners.
How real estate investors and multi-entity owners use the Section 469 grouping election under Reg 1.469-4 to aggregate hours across properties and release suspended losses — covering the appropriate economic unit test, the Reg 1.469-9(g) real estate professional aggregation, Rev. Proc. 2010-13 disclosure rules, and why the election is easier to file than to undo.
Section 162(l) lets sole proprietors, partners, and more-than-2% S-corp shareholders deduct 100% of medical, dental, vision, and long-term care premiums above the line on Schedule 1, Line 17—if they clear the earned-income cap, the spouse-employer rule, and the W-2 reporting choreography on Form 7206.
A 2026 field guide to Section 162(a)(2) travel deductions — how the tax home rule, the temporary-vs-indefinite test, and the one-year rule determine whether consultants, traveling nurses, and other mobile workers can deduct lodging, meals, and per diem.
Section 174A restores immediate domestic R&E expensing and lets small businesses with $31 million or less in average annual gross receipts amend 2022, 2023, and 2024 returns for refunds — but the retroactive election must be filed by July 6, 2026.
