Appreciated-asset donation pitches: the deduction is real, the appraisal usually isn't

Primary sources: IRC §170; Treas. Reg. §1.170A; qualified appraisal rules (IRC §170(f)(11))

The honest short answer

Donating appreciated assets you've held more than a year is one of the cleanest strategies in the code: deduct fair market value, and never pay capital gains on the appreciation. The schemes take that legitimate skeleton and attach a fantasy number to it — buy an asset cheap (art, collectibles, land interests, obscure inventory), obtain a friendly appraisal at 4–10× what you paid, donate, and deduct the invented value. The IRS has an entire enforcement program aimed at exactly this, with a qualified-appraisal regime, valuation penalties up to 40%, and promoter investigations behind it.

What's legitimately true in the pitch

FMV deduction, no gains tax: long-term appreciated stock donated to charity is textbook, efficient, and audit-boring. We recommend it constantly.
Bunching works: stacking donations into a donor-advised fund in high-income years is real planning.
Unusual assets can be donated — with a genuinely independent qualified appraisal and Form 8283 done right.

Where the pitches mislead

The value is the product. If the strategy only works because the appraisal says $500,000 for something you bought this year for $80,000, the strategy is the appraisal — and the IRS knows how to read a purchase date.
Short holding periods quietly cap you at cost. Property held one year or less is generally deductible at basis, not FMV — a detail many packaged deals bury.
"Our appraiser is included." An appraiser supplied by the promoter, paid per deal, valuing every unit at the same convenient multiple, is a red flag the size of the deduction.
You carry the penalties, not the promoter. Gross valuation misstatements bring a 40% penalty on top of the tax — payable by you, years later, while the promoter is on to the next product.

Questions to ask before you sign

Would an unrelated buyer actually pay the appraised amount tomorrow, in cash?
Who selected and paid the appraiser, and what do they earn per transaction?
Have I held this asset more than a year — really?
Why does the charity want this asset, and what will they do with it?

Our position: donate appreciated stock all day. The moment a deal's return depends on an appraisal exceeding what you just paid, you're not doing charitable planning — you're buying a penalty with a delay on it.

Been shown a donation deal with a big multiple?

Bring us the offering and the appraisal before you sign the 8283. We'll tell you what survives scrutiny and what the penalty math looks like if it doesn't.

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This review discusses a category of investment and tax marketing generally, not any specific company or offering, and is not investment, legal, or tax advice for any particular situation.