#capital-gains
Track and report capital gains from investments
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.
Incentive Stock Options and Non-Qualified Stock Options trigger taxes at different events and rates. This guide covers the AMT trap, qualifying vs. disqualifying dispositions, the $100,000 ISO vesting limit, and eight strategies tech workers use to lower the tax bill on equity compensation.
NFTs are taxed as property under US rules. Long-term gains on collectible NFTs are capped at 28%, creator sales are ordinary self-employment income, and Form 1099-DA reporting from marketplaces begins with 2025 transactions. This guide covers the math, the forms, and the moves to make before filing.
A 2026 guide to Section 1202 QSBS for founders, early employees, and angel investors — eligibility tests, the new $15M cap and tiered holding periods under OBBBA, stacking with non-grantor trusts, state conformity gaps in California and Pennsylvania, and how to claim the exclusion on Form 8949.
Section 1031 lets real estate investors defer capital gains and depreciation recapture by swapping investment properties, but only when the 45-day identification window, 180-day closing deadline, qualified intermediary rules, and post-TCJA like-kind requirements are followed exactly.
A plain-English guide to IRS Section 1091 — the 61-day window, what counts as "substantially identical," the IRA trap that destroys losses permanently, the current crypto exemption, and how to report a wash sale on Form 8949.
Complete guide to cryptocurrency tax compliance using Beancount.io. Master IRS requirements, automate tax reporting, optimize capital gains, and ensure accurate crypto tax filing.
