Tax Reference

Investments & Capital Gains

Capital gains rates, loss harvesting, crypto taxation, NIIT, QSBS, and charitable giving strategies.
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Investment taxation is where planning decisions compound most visibly. The difference between short-term and long-term rates, the wash sale rule, the NIIT surcharge, and the complete absence of wash sale rules for cryptocurrency all create planning opportunities that are impossible to exploit without understanding the mechanics.

Capital Gains
Calculator
Capital Gains Calculator
Federal capital gains tax with NIIT and state.
Guide
Tax Loss Harvesting
Wash sale rule, netting, $3K offset, crypto exception.
Guide
NIIT Guide
3.8% net investment income tax - thresholds and planning.
Guide
Section 1202 QSBS
100% gain exclusion on qualifying C-corp stock.
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§1411 NIIT Net Investment Income Tax
3.8% surtax. Thresholds NEVER indexed: $200K single, $250K MFJ, $125K MFS. Trust $16,000 (2026). Form 8960. Material participation tests. §1.1411-10(g) CFC election. Bruyea treaty FTC.
Guide
Opportunity Zones 2.0 (OBBBA 2027)
OBBBA made QOZ program permanent. New 2027 designation round (decennial cycle). Rolling 5-year deferral. 10% urban / 30% rural QROF basis step-up. 50% rural substantial improvement (immediate). 70% MFI test. 125% MFI cap. Year-30 FMV freeze.
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QSBS §1202 OBBBA Graduated Exclusion
Stock issued after 7/4/2025: 3-tier exclusion (50% at 3yrs, 75% at 4yrs, 100% at 5yrs). Per-issuer cap $15M (up from $10M). Gross asset threshold $75M (up from $50M). 28% rate trap on partial exclusion. §1202(i) no rollover for pre-OBBBA stock. State conformity gaps. §1045 rollover. Stacking strategy.
Cryptocurrency
Guide
Crypto Tax Guide (2026)
HIFO/FIFO, staking Rev. Rul. 2023-14, Form 1099-DA, wash sale exception.
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Crypto Basics
Property classification, taxable events, record-keeping.
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Form 1099-DA: Digital Asset Broker Reporting
§6045 digital asset broker reporting effective 1/1/2025. 2025 gross proceeds only; 2026 adds basis for covered assets. T.D. 10000 / T.D. 10021. Rev. Proc. 2024-28 wallet-by-wallet basis mandate. Universal accounting eliminated. DeFi rules VACATED by Congressional Review Act March 2025. Notice 2024-56 / Notice 2025-33 transition relief through 2027. Stablecoin and NFT de minimis. Form 8949 reconciliation.
Charitable Giving
Guide
Charitable Giving Strategies
DAF, CRT, CLT, QCD $108K, appreciated property, bunching.
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Charitable Deduction Guide
AGI limits, substantiation, noncash contributions.
Additional Resources
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Stock Options Tax
Covered calls, §1256 index options 60/40, straddle rules.
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Investment Interest §163(d)
Margin interest limited to net investment income; Form 4952.
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QSBS §1202
100% capital gains exclusion after 5 years; $10M limit.
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§1244 Small Business Stock
$100K ordinary loss on failed startup vs. $3K capital loss limit.
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RSU & Restricted Stock
Vesting income, withholding shortfall, basis trap.
Guide
Collectibles: 28% Rate
Art, coins, gold ETFs, precious metals - 28% vs 20% LTCG.
Guide
Crypto Staking, DeFi & NFTs
Rev. Rul. 2023-14, NFT collectibles, Form 1099-DA, HIFO basis.
Guide
Foreign Currency §988
Ordinary income/loss, §988(e) capital election, hedging exclusion.
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