Educational reference only — not tax, legal, or investment advice. Examples use 2025–2026 federal rates and are illustrative.
Chapter 5

Use Cases by Asset Type

How the SIS applies to real estate, business sales, farms, professional practices, and other capital assets.

This is a single chapter of the full Structured Installment Sale knowledgebase. Open the full version for search, the reading-level toggle, and all 12 chapters side by side.

Chapter 5

Use Cases by Asset Type

Where the SIS fits — investment and commercial real estate, residences, businesses, and other assets.

In plain English

The SIS works for almost any appreciated capital asset sold for a large gain — a rental, an office building, a company, a farm, a professional practice. It does not work for things the code excludes from installment reporting, such as publicly traded stock, inventory, or dealer property. The best candidates have a clean capital gain, limited recapture, and an owner who wants steady income rather than a lump sum.

Investment real estate

Rental and investment property is the most common SIS use case. A long-held rental with substantial appreciation generates a large long-term gain the SIS can spread to manage brackets and avoid NIIT. The key planning point: unrecaptured §1250 gain is deferrable but taxed at a maximum 25% rate when recognized, and any §1245 recapture is taxed in full as ordinary income in the year of sale.

Commercial real estate (partial SIS)

Commercial sellers frequently use a partial SIS: take part of the price in cash at closing (for liquidity or debt payoff) and structure the remainder. For transactions whose deferred obligations exceed $5 million at year-end, the §453A interest charge becomes a cost factor to model.

Primary residence & the §121 exclusion

A primary-residence sale can combine the SIS with the IRC §121 exclusion of $250,000 (single) or $500,000 (married). The excluded gain is tax-free; the SIS then spreads the taxable gain above the exclusion. In MetLife's illustration, a $4.25M Florida home with a $2.15M gain, applying the $250K exclusion and structuring the balance over 15 years, avoids NIIT and saves ~$115,250 in combined federal tax.

Sale of a business

  • Asset vs. stock sale & §1060 allocation. In an asset sale, price is allocated across asset classes; goodwill and going-concern value are capital and SIS-eligible, while inventory and recapture items are not.
  • Goodwill — typically the largest piece of a practice or service business — is a clean capital asset ideal for structuring.
  • §1202 QSBS may already enjoy gain exclusion; sellers coordinate it with structuring of non-excluded gain.
  • §453B(h) allows S-corporation shareholders to continue installment reporting in qualifying liquidations.

Other assets

Farmland is an excellent SIS asset — often a clean gain (with stepped-up basis if inherited) and exempt from the §453A interest charge. Vacant land, vacation/second homes, professional practices, and art/collectibles (taxed at up to the 28% collectibles rate) also qualify. Publicly traded securities, crypto treated as marketable, inventory, and dealer property cannot use the installment method.

Who is a good fit — and who is not

Good fitPoor fit
Long-term gain of roughly $500,000+Small gains where setup cost outweighs benefit
Low-to-moderate other income (room under NIIT)High ongoing salary/business income
Clean capital asset (goodwill, land, clean real estate)Heavily depreciated property with large recapture
Wants guaranteed long-term income; patientNeeds full proceeds immediately
Cooperative buyer willing to use the addendumAll-cash buyer unwilling to engage
High-rate environment (lock in favorable yield)Wants market upside on the proceeds
↑ Back to top
← Open in full knowledgebase
Put it to work

See the numbers for your own sale.

The knowledgebase is the theory. The calculator and an advisor turn it into your numbers.