Sell appreciated asset inside CRT — no cap gains, income stream for life, remainder to charity.
Contribute appreciated stock/real estate/business to a CRUT: trust sells tax-free, invests proceeds, pays you 5–10% annual income for life (or term ≤20 yrs). Immediate charitable deduction of PV of remainder (10–40% of contribution). At death/term, remainder passes to named charity. Distributions taxed under 4-tier ordering rules (ord income → cap gains → tax-exempt → return of principal).
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Bunch 5 years of giving into one DAF contribution, itemize once, then take standard deduction.
Give appreciated stock — no cap gains, full FMV deduction, and rebuy with cash to reset basis.
Zeroed-out CLAT: charity gets annual payments, heirs get remainder gift-tax-free.
Direct up to $105K/yr from IRA to charity — counts toward RMD, NOT in AGI.
Fund a family foundation for legacy giving, employ next gen, control grants forever.
Donate development rights on land → charitable deduction of full easement value.
Donate the facade of a historic building — deduction ~10–15% of building value.
Contribute to a charity-managed pool — get pro-rata income for life + charitable deduction.