What to hold in taxable, tax-deferred, and Roth accounts to minimize lifetime taxes.
Federal, state, municipal — three different tax treatments to understand.
Short-term (ordinary rates) vs. long-term (preferential rates) and the 1-year holding line.
FIFO, LIFO, specific identification — and why specific ID is usually best.
The federal exemption, annual gift exclusion, and what happens at the state level.
The 3.8% surcharge above income thresholds, often overlooked in planning.
Donate from your IRA after 70½ to satisfy RMDs without recognizing income.
The 60-day holding rule that determines whether dividends get low or high tax rates.
Filling up lower tax brackets in early retirement or low-income years.
Why holding appreciated assets until death can erase decades of gains for heirs.
Selling losers to offset gains and ordinary income — and the wash-sale rule that ruins it.
30-day window that disallows losses on substantially identical securities.