Big Sale TaxHans Goldstein: Tax & Exit Planning
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Nine ways to exit, side by side.

Cash, a Section 453 installment sale, 1031, combinations, Opportunity Zones, deferred sales trust, Delaware statutory trust and a charitable remainder trust, run through the same tax engine on one illustrative sale.

Worked example

One sale, nine outcomes.

Pick a metric, then tap a scenario for the year-by-year detail. Status shows whether a scenario is computed by the engine, illustrative (engine plus labeled assumptions) or qualitative.

Loading scenarios.

Assumptions and method
  • One seller couple, married filing jointly, California residents, both age 66 (senior deduction through 2028 per the engine).
  • Commercial building held as a rental (not a real estate professional): gains and rent are subject to the 3.8% net investment income tax.
  • Sale price $5,000,000, closing early in 2026 so year 1 is the full 2026 tax year.
  • Selling costs $230,500 (engine closingCosts: 4% commission, 0.5% escrow and title, $5,500 county transfer tax).
  • Adjusted basis $1,500,000 after $800,000 of straight-line depreciation (all unrecaptured Section 1250 gain, 25% maximum rate; no Section 1245 recapture). Total gain $3,269,500.
  • Mortgage $1,000,000 at 6.5%, paid off at closing in every path unless stated.
  • Other ordinary income $150,000 a year and Social Security $50,000 a year combined, flat for 20 years (no inflation). No suspended passive losses, no capital loss carryovers.
  • Horizon 20 years (2026 through 2045). Anything still held is sold in January 2046 and that tax is subtracted.
  • Money not otherwise invested sits in one taxable account earning 5% a year before tax; every year's earnings are taxed as ordinary investment income through the engine (conservative for a stock portfolio). A negative balance means borrowing from other assets at the same 5%.
  • Buyer notes: level annual payments, first payment December 2026. Installment and boot notes 6.00% (10 or 20 years); deferred sales trust note 5.25%. All at or above the highest 2026 long-term AFR (5.22%, 2026-10).
  • Replacement real estate (1031 and Delaware statutory trust) returns 5% before tax: 3.5% net cash yield after expenses and reserves plus 1.5% yearly growth, the same 5% as the account. New $1M loan at 6.5% interest only.
  • Federal and California tax tables: 2026 (Rev. Proc. 2025-32, OBBBA) carried forward unchanged to later years by the engine; California 2025 schedules projected. California's top brackets are kept in every year.
  • Taxes shown are the extra tax the sale path causes above the no-sale baseline (other income and Social Security alone).
  • Medicare IRMAA surcharges (both spouses, two-year lookback) are reported separately and not included in tax or value.
  • Illustrative only, not tax advice. Default risk on buyer notes, fund risk and trust investment risk are not modeled.

Every year 2026 to 2045 is priced with SIS.yearTax from the Big Sale Tax engine (engine.js) on that year's whole stack: other income, Social Security, the path's own items (gain by character, note interest, rent, trust payouts, Opportunity Zone inclusions) and the investment account's earnings. Federal regular tax, AMT, NIIT, the senior deduction and California are all from the engine. Cash flows: closing cash earns from closing; note payments, rent and trust payouts arrive at year end; each year's tax is paid at that year's end. "year1_tax" and "deal_tax" exclude tax on the investment account's earnings; "tax" and "total_tax_nominal" include it plus the January 2046 sale of anything still held. "after_tax_value_horizon" = account balance at the end of 2045 + after-tax proceeds of anything still held. Script: ~/sites/bigsaletax/tools/scenarios.js.

Convention: Year-end tax convention: every year's tax, including the year-1 sale tax, is paid at the end of that year (the convention recommended in the 10/1/2026 engine timing audit); closing cash earns from closing. Using one convention for every path keeps the cash sale from being penalized for paying its tax earlier than the others.

Illustrative only. Your numbers will differ. Not tax or legal advice.

Quick matrix

The four most common paths.

Cash saleInstallment sale1031 exchangeOpportunity Zone
What it defersNothingGain as payments arriveGain reinvested in like-kind real estateOnly the gain you invest, within 180 days
Who holds the moneyYouThe buyer, under your noteQualified intermediary, then the new propertyThe Opportunity Zone fund
Main trade-offBiggest one-year taxBuyer credit risk, managed with security and termsMust buy real estate, all proceeds and debtIlliquid, long hold for the full benefit
Best fitSmall gain or high basisSeller willing to be the bankOwner staying in real estateAny capital gain, ten-year horizon

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The Big Sale Tax Analysis is a flat $5,000. Start with a free scoping call; you are invoiced only after it, and only if you go ahead.

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