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#tax-deductions

Tax Deductions

Maximize tax deductions and reduce your tax liability legally

FDII and Form 8993: How U.S. C Corporations Hit a 13.125% Effective Tax Rate on Foreign Sales

A working guide to the FDII (now FDDEI) deduction on Form 8993 — which U.S. C corporations qualify, how the Section 250 math drops the effective federal rate to 13.125% on foreign-derived income, the taxable income limitation, documentation the IRS expects, and how OBBBA simplifies the calculation starting in 2026 by removing the QBAI step and expense allocations.

Form 8283 Noncash Charitable Contributions: A Donor's Guide to the $5,000 Qualified Appraisal Threshold and IRS Substantiation Rules

Form 8283 is required when total noncash charitable contributions exceed $500. Above $5,000, donors need a USPAP-compliant qualified appraisal and three signatures on Section B; over $500,000 the full appraisal attaches to the return. Section 170(o) can claw the deduction back if the charity disposes of tangible property within three years, and the 40% gross valuation misstatement penalty has no reasonable-cause defense.

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.

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 170(h) Conservation Easement Deductions: Why High-Income Donors Face 40% Penalties, Automatic Audits, and a 6% Court Allowance Rate

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 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.