Structured Installment Sale — Side-by-Side Comparison

5% Return • 2025 MFJ LTCG (simplified) • 5/10/15/20/30 yrs

This tool compares two simple paths for a one-time sale:
1) Pay tax now and invest what’s left, versus 2) Use a Structured Installment Sale, pay a small implementation fee, get interest-only payments each year, and pay the long-term capital gains tax at the end when the principal is paid back. This calculator models a Structured Installment Sale funded through an assignment/annuity company — it is not a Deferred Sales Trust.

We’ll assume this is the taxable long-term gain. Max $50,000,000.
Interest-only during the term; principal is paid back at the end.
Used for both paths for a fair comparison. If unsure, leave at 5%.
What we assume 2025 long-term capital gains brackets (MFJ, simplified) • Ignore NIIT & state taxes • Same growth rate for both paths • Structured Installment Sale implementation fee is taken out upfront.
What do these terms mean?
Pay tax now: You pay the long-term capital gains tax today and invest what remains. Your money grows at the rate you entered.
Structured Installment Sale: You pay a one-time implementation fee (1% of sale, min $2,500, max $10,000). The rest is used to fund the structured sale and earns the same rate. Each year you receive interest-only payments. At the end, you receive the principal back. That’s when the long-term capital gains tax on the gain is due.
Why keep the rates the same? To keep this a straight apples-to-apples comparison. We’re looking only at the timing of taxes and the structured sale fee — not trying to predict investment outperformance.