A charitable remainder trust lets you sell an appreciated building with no tax due at closing, reinvest every dollar, and collect income for life. The trade: what is left goes to a charity you pick, not your kids, and the tax does not disappear. It reaches you a slice at a time, in an order the tax code sets.
In this solo episode of The Tax Strategy Playbook, David Wiener, Mr. Cash Flow, explains how a charitable remainder trust works in plain English: the charitable remainder annuity trust (CRAT) versus the charitable remainder unitrust (CRUT), and why the flip unitrust is built for real estate. You'll see the tier system that decides how your payments are taxed, what happens to years of depreciation inside the trust, and the rule that shrinks your charitable deduction on a building that has had a cost segregation study. Then one fourplex runs two ways, sold outright or put in a trust first, as a labeled illustration.
You'll also get the 2026 charitable deduction changes (a floor of 0.5% of AGI for itemizers, a 35% benefit cap for the top bracket, and a new $1,000 or $2,000 deduction for people who don't itemize), year-end moves with a donor advised fund and appreciated stock, the Hoensheid Tax Court case on giving too late, why a mortgage causes trouble, and the annuity scheme the IRS treats as abusive. A properly drafted charitable remainder trust is settled law. That annuity version is not.
Built for the real estate investor who would sell tomorrow if not for the tax bill, the business owner planning year-end giving, and the tax professional who will field 2026 charitable deduction questions this filing season.
*CHAPTERS*
00:00 Charitable remainder trust explained: sell a $1.3M building with no tax at closing
03:11 What is a charitable remainder trust? CRAT vs CRUT vs flip unitrust
07:15 Charitable remainder trust taxation: the tier system and your depreciation
10:35 Charitable deduction changes for 2026: the 0.5% floor, 35% cap, donor advised funds
15:04 Donating a cost segregated building: how depreciation recapture cuts the deduction
19:32 Sell a rental outright vs charitable remainder trust: a fourplex example
25:33 Charitable remainder trust mistakes: timing, debt, appraisal, self-dealing
29:12 Charitable remainder trust myths and the abusive CRAT annuity scheme
32:11 Who should use a charitable remainder trust? CRT vs 1031 exchange vs DST, plus FAQ
40:00 Charitable remainder trust playbook: 5 steps before you sell
Nothing in this episode is tax or legal advice for your situation. This is education, and your facts need your own tax professional and an estate attorney working together. Tax evasion is a crime, but tax avoidance is mandatory.
Your host: David Wiener, "Mr. Cash Flow"
https://davidhwiener.com
mailto:David.wiener@cashflowstrategies.us
770-224-8504x2
Schedule a conversation or free consultation at
https://calendly.com/david-wiener/initial-consultation
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