Big sale options: what you want, what fits, and the risk
Start with your goal. See which way of selling usually fits it, and the one honest risk that comes with it.
By Hans Goldstein (Enrolled Agent, admitted to practice before the IRS) · Updated
The best way to sell is not the one with the lowest tax bill. It is the one that fits what you want the money to do. Start with the goal, then look at the one risk that comes with each path. Rules are 2026 federal law, checked October 15, 2026; each linked page names its sources.
What you want, what usually fits, and the main risk
| If you want | It usually fits | The main risk |
|---|---|---|
| All cash now, and simplicity | Cash sale Installment sale vs cash sale | The whole gain is taxed in one year, often at the top long-term rate plus the 3.8% surtax, and you cannot undo it. |
| Buy more real estate | 1031 exchange 1031 exchange | Strict clocks: 45 days to identify and 180 days to close, real property only, and the tax is postponed rather than erased. |
| Steady income and lower brackets without being the bank | Structured installment sale Two kinds of installment sales | Payments are fixed once set and cannot be sped up, they depend on the insurance company's strength, and it must be set up before closing. |
| Top price, and you are willing to be the bank | Seller-carried installment sale Seller-carried note | The buyer's credit and the property carry the risk. If payments stop, you foreclose and take the property back. |
| Give to charity and keep income | Charitable remainder trust Charitable remainder trust | The gift is permanent and the trust is irrevocable, at least 10% of the value must go to charity (IRC 664(d)), and setup and administration cost money. |
| Leave it to heirs | Hold for the step-up in basis, or borrow against it Step-up at death | Holding keeps all your eggs in one asset and you still own its risk. Borrowing adds interest cost and can be called or repriced if rates or values move. |
| Passive real estate after selling | Delaware statutory trust through a 1031 exchange Delaware statutory trust | You give up control, the interest is hard to sell, sponsor fees apply, and a property loss can reduce what you put in. |
| Defer the gain and invest it in a qualified community | Opportunity Zone fund Opportunity Zones 2.0 | Money is locked in one fund for years, the fund can lose value, and the deferred tax still comes due when the deferral ends. |
"Usually fits" is a starting point, not a recommendation. Your asset, basis, debt, state, age and timing can change the answer, and some paths combine, for example a 1031 exchange with part of the proceeds taken as an installment note.
The two installment sales, side by side
Both use Section 453, so the gain is taxed as you are paid. The difference is who pays you. A seller-carried sale makes you the bank. In a structured installment sale the buyer pays in full at closing and an insurance company pays you on the schedule you choose. Read the side-by-side table, and run your own numbers, on two kinds of installment sales, same tax math.
If you are retiring with stuck losses
Old suspended passive losses and capital loss carryovers can change which option nets the most, and an installment sale spreads the loss release along with the gain (IRC 469(g)(3)). See stuck losses when you retire, with a dated example.
Next step
Want to know which row fits your sale? Book the free scope call. It is a short call to see whether the $5,000 Big Sale Tax Analysis is worth it for you. Only the scope call is free, and there is no obligation. You can also try the exit strategy finder, which asks 12 questions and ranks the paths for your goal.
Frequently asked questions
Which way of selling a big asset is best?
It depends on your goal. Cash fits simplicity, a 1031 exchange fits staying in real estate, an installment sale fits steady income and lower tax brackets, a charitable remainder trust fits giving and income, and holding fits heirs. Each has a main risk, listed in the table above.
What is the difference between a seller-carried and a structured installment sale?
Both spread the gain under Section 453. In a seller-carried sale the buyer owes you and you take the credit and property risk. In a structured installment sale the buyer pays in full at closing and an insurance company makes the payments, so the risk moves to the insurer's strength and a fixed schedule. See the side-by-side page.
Can old losses change which option is best?
Yes. Capital loss carryovers offset gain without a cap, and a sale of your entire interest to an unrelated party releases suspended passive losses (IRC 469(g)(1)(A)). A large bank of either can shrink the tax a deferral path would save.
Hans Goldstein is an Enrolled Agent, admitted to practice before the Internal Revenue Service. Not affiliated with or endorsed by the IRS. General education, not tax or legal advice for your situation.
Also free: the book Same Sale, Different Tax, the same $1,000,000 gain taxed ten ways. Want it run on your sale? Book a free scope call to see whether the Big Sale Tax Analysis is worth it.
Who you will talk to
Hans Goldstein · Sacramento, California
Hans Goldstein: Tax & Exit Planning, an independent practice. Enrolled Agent, admitted to practice before the Internal Revenue Service. CA Insurance License #4273294, NPN 20602398.
- What happens first
- You fill in the short form for a free scope call, about 5 minutes. Hans reviews every one personally and replies within 1 business day. If it is a fit, you get a link to book the call.
- The scope call
- Fifteen minutes, free: price, timeline, what you are selling and what the money is for. Scope means you hear whether the analysis is worth it for your sale.
- What you get
- A written side-by-side comparison of your cash-sale baseline against every path that fits, year-by-year numbers, a written recommendation, and a review meeting with you and, if you like, your CPA and attorney.
- What it costs
- The scope call is free. The Big Sale Tax Analysis is $5,000 per household per transaction, only if you decide it is worth it. No retainer, no hourly billing, no obligation to use any strategy.
- How Hans is paid
- The $5,000 fee pays for analysis only and is not reduced or credited if you buy anything. You are never required to buy anything. No referral fees are paid to or received from brokers, CPAs or attorneys. Hans is also a licensed insurance producer with a separately owned insurance business. That business is not part of this engagement, and the analysis does not recommend insurance products. If you later choose an installment sale funded through an insurance company, that company pays Hans a commission through his separate insurance business. He may be compensated by that business if you use an insurance-funded installment sale. Hans is an Enrolled Agent (EA), admitted to practice before the Internal Revenue Service. He is not a CPA, attorney or registered investment adviser; the analysis models tax effects and does not recommend specific securities. Read the disclosures.
Book a free scope call or call 213-340-2018. Hans answers or calls back the same business day.
Know your number before you sign.
Start with a free scope call: a short call to see whether the Big Sale Tax Analysis is worth it for your sale. No obligation.
Prefer email? Request the analysis by email.
You talk to Hans Goldstein. Enrolled Agent, admitted to practice before the IRS.