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.
The 3.8% Net Investment Income Tax kicks in once MAGI crosses $200,000 single or $250,000 joint—thresholds frozen since 2013. This guide explains who pays NIIT, how Form 8960 calculates it, which income types count (interest, dividends, capital gains, passive rentals) and which don't (wages, IRA distributions, muni interest), plus planning levers to cut exposure.
How Qualified Opportunity Funds defer capital gains, deliver tax-free appreciation after a 10-year hold, and what changes for new investments under OBBBA's permanent Opportunity Zones 2.0 rules starting January 2027.
Section 1014 of the Internal Revenue Code resets an inherited asset's cost basis to its fair market value on the date of death, erasing the decedent's lifetime appreciation from the tax base — a provision the Joint Committee on Taxation estimates will cost the federal government $72.5 billion in 2026.
A Section 83(b) election lets founders and early employees pay ordinary income tax on the grant-date value of restricted stock instead of on each vesting tranche, shifting future appreciation into long-term capital gains. The 30-day filing window is absolute and starts on the actual transfer date.
How qualified versus disqualifying dispositions change the tax bill on a Section 423 ESPP, with worked examples covering ordinary income, adjusted basis, Form 3922 cost-basis fixes, and a decision framework for when holding two years actually pays off.
Take control of your finances with our open-source double-entry accounting system. Start your ledger today.
© 2019 - 2026 Beancount.io
