Appreciated assets held until death get FMV cost basis — heirs pay $0 cap gains on lifetime appreciation.
IRC §1014 gives inherited assets a basis equal to date-of-death fair market value. A $100K stock originally purchased for $10K becomes $100K basis in the heir's hands — the $90K of lifetime gain is permanently erased. Combined with the $13.99M estate exemption, HNW families can pass millions with zero income OR estate tax. Strategy: hold your MOST appreciated positions; sell high-basis or losing positions for liquidity. In community-property states, both halves get stepped up at first death (double step-up).
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Multiply the $10M §1202 exclusion across multiple trusts.
4% corporate tax + 0% capital gains for bona fide residents.
Stack the $500K primary-home exclusion on top of a 1031 deferral.
Convert Traditional to Roth during sabbaticals or business-loss years.
Capitalize property taxes and interest on undeveloped land.
Deduct now, control forever, employ heirs.
Ordinary loss (not capital loss) on failed small biz — up to $100K.
Buy leveraged real estate inside your IRA — tax-deferred or tax-free.