The One-Year Rule
The single most impactful tax strategy: holding for at least one year and one day converts short-term gains (taxed up to 37%) into long-term gains (taxed at 0–20%). This one decision can cut your tax bill in half.
The 0% Bracket Opportunity
In 2025, single filers with total income under $48,350 pay zero federal tax on long-term gains. Retirees, early FIRE practitioners, and anyone in a temporarily low-income year can strategically realize gains completely tax-free. This is one of the most underutilized strategies in personal finance.
Tax-Loss Harvesting Mechanics
Harvesting losses offsets capital gains of the same type first (long vs. short), then crosses over, then reduces ordinary income by up to $3,000 per year with indefinite carryforward. The key risk: the wash-sale rule disallows losses if you repurchase the same or substantially identical security within 30 days before or after the sale.
Depreciation Recapture on Real Estate
Every year you claim depreciation on a rental property reduces your cost basis. When you sell, the IRS "recaptures" those deductions at a maximum 25% rate, regardless of your income level. A 1031 exchange defers this tax indefinitely along with the capital gain.