#capital-gains
Track and report capital gains from investments
U.S. digital asset brokers must issue Form 1099-DA for sales after December 31, 2024. This guide explains what each box reports, why 2025 forms cover only gross proceeds while 2026 forms add cost basis, and how to reconcile broker data with your own records on Form 8949.
How IRC Section 453 and Form 6252 let sellers spread capital gain on seller-financed real estate or business sales across the years payments arrive — including the gross profit percentage formula, the depreciation recapture trap, the Section 453A interest charge on installment balances above $5 million, and when to elect out.
When a C corp converts to an S corp, Section 1374 imposes a 21% corporate tax on appreciated assets sold within 5 years.
Section 1042 of the IRC lets a C-corporation owner selling shares to an ESOP defer federal capital gains tax indefinitely — and potentially eliminate it through step-up at death. This guide covers the five qualifying conditions, what counts as Qualified Replacement Property, the floating-rate-note diversification strategy, and the trade-offs founders should weigh against a strategic sale.
How a Charitable Remainder Trust lets you sell appreciated assets without capital gains tax, take an immediate income tax deduction, collect lifetime income, and pass the remainder to charity—plus the math comparing CRUT, CRAT, NIMCRUT, and Flip CRUT structures under the May 2026 5.0% Section 7520 rate.
Form 4797 governs every business property sale outside Schedule D and decides whether your gain is ordinary or capital. This guide walks through Section 1245 and 1250 recapture, the Section 1231 five-year lookback rule, the 25% unrecaptured Section 1250 gain rate, and seven mistakes that trigger CP2000 notices.
How the federal kiddie tax pulls a child's unearned income above $2,700 in 2026 onto the parent's marginal rate via Form 8615. Mechanics, UTMA/UGMA pitfalls, full-time-student rules through age 23, and planning strategies using 529 plans, Roth IRAs, and gain timing.
The Net Unrealized Appreciation election lets retirees pay long-term capital gains rates on employer stock distributed from a 401(k) instead of ordinary income, often saving more than $144,000 on a $1 million position. Covers eligibility under IRC 402(e)(4), the lump-sum distribution rule, and the most common mistakes that destroy the strategy.
A reverse 1031 exchange lets a real estate investor close on a replacement property before selling the relinquished one by parking title with an Exchange Accommodation Titleholder under Revenue Procedure 2000-37's safe harbor. The taxpayer must identify the relinquished property within 45 days and complete the swap within 180 days, with no extensions. EAT fees typically run $5,000 to $15,000 above a forward exchange, so the deferred gain needs to be large enough to justify the cost.
How Section 121 lets U.S. homeowners exclude up to $250,000 ($500,000 for joint filers) of capital gains on a primary home sale — covering the 24-month ownership and use tests, the two-year frequency rule, partial exclusions, depreciation recapture, and the nonqualified-use allocation.
Year-round tax loss harvesting can add 0.5%–1.5% in annual after-tax returns to a taxable portfolio. This guide explains the IRS netting order, the wash sale rule across taxable and IRA accounts, and a practical framework for harvesting short-term losses without losing the deduction.
An asset sale vs stock sale changes who pays tax, who carries liability, and how a deal closes. Compare 2026 tax math, successor liability doctrines, and the S-corp hybrid structures — Section 338(h)(10) and F-reorganizations — that now dominate mid-market deals.
