Both defer the tax on a sale and turn it into income, but they're built for different people. One is for sellers who want flexibility and their heirs to keep the principal; the other is for the charitably inclined. Below is the honest comparison.
If you're selling an appreciated asset and want to defer the tax while creating income, you'll likely hear about both a structured installment sale (SIS) and a charitable remainder trust (CRT). They sound similar but serve different goals. This is how to choose.
Send me the sale price and rough basis. Within one business day I'll email you the actual number and the Seller's Guide to §453. If it doesn't fit your deal, I'll tell you that plainly.
No retainer · no obligation. Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
Go deeper: an independent analysis of the charitable remainder trust on Big Sale Tax.
| Structured Installment Sale (§453) | Charitable Remainder Trust | |
|---|---|---|
| How it defers | Spread proceeds & gain over years | Sell tax-free inside the trust; income for life/term |
| Who gets the remainder | You / your heirs (it's your money) | A charity keeps the remaining principal |
| Charitable intent required? | No | Yes, that's the point |
| Revocable? | Schedule is fixed once set | Irrevocable |
| Upfront charitable deduction? | No | Yes (partial) |
| Complexity / cost | Lower | Higher (trust, trustee, admin) |
| Income backing | Assignment company, funded by a fixed annuity from a highly rated life insurer | Trust's own investments |
You genuinely want to benefit a charity, want an upfront charitable deduction, and are comfortable that the remaining principal goes to that charity rather than your heirs at the end.
You want to keep the money in your family, want simplicity, don't have a charitable goal, and want fixed payments from an assignment company funded by a fixed annuity, rather than depending on trust investment performance.
Both are legitimate. The deciding question is simple: at the end, do you want the principal to go to a charity (CRT) or to your family (SIS)? Run your numbers on both before deciding.
With a structured installment sale, the proceeds and remaining value stay yours and pass to your heirs. With a charitable remainder trust, a charity keeps the remaining principal after your income term ends. Both defer the tax and create income.
Yes. A charitable remainder trust is designed for people who want to benefit a charity. If you have no charitable intent and want your heirs to keep the principal, a structured installment sale is usually the better fit.
A structured installment sale is generally simpler and less expensive. There's no irrevocable trust to create, fund, and administer. A CRT involves trustee and administration costs.
A CRT provides an upfront partial charitable deduction and tax-free sale inside the trust, but you give up the principal to charity. A structured installment sale defers tax without giving away the principal. 'Bigger' depends on whether the charitable gift aligns with your goals.
A structured installment sale's payments are fixed by contract: the assignment company owes them and funds them with a fixed annuity from a highly rated life insurer. A CRT's income depends on the trust's own investment performance.
Before you sign anything, run your numbers with someone who structures the deal to be tax-smart and audit-ready from day one.
Call 213-414-2808 Run the Numbers →
A plain-English guide for sellers on how a structured installment sale defers the tax when you sell a business, practice, or property. It covers the math, the alternatives, and how to tell if your deal fits.
Leave your details and the PDF downloads right away. Within one business day Hans will email a preliminary read on which structure fits your deal. No retainer. On a funded structure, the insurer pays a one-time commission of about 4% of the amount structured to the brokerage firm that places it (Hans’s share is about 2.4%; no trail). It is built into the annuity pricing, not a separate fee.
📞 Hans Goldstein · 213-414-2808 · CA Insurance License #4273294 · Independent §453 specialist · Goldstein & Co. LLC
Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
