Start simple. Get nuanced when you need to. Every calculator below uses honest math, different layers of detail for different situations.
The fast one. Two scenarios (0% yield + 4% yield) side-by-side. Configurable §121 exclusion, depreciation recapture, prior-1031 basis. Most sellers only need this to get the gist.
The most accurate California SIS calculator on the internet. Asset-type selector (real estate / business / stock / partnership). §1202 QSBS · §1245/1250 recapture · IRMAA tiers · CA MHST · non-resident withholding · cap-loss carry · CPA breakdown · year-by-year schedule · IRR · break-even yield · "math we are mathing" formulas. GUL/IUL legacy overlay with age advisor.
If you take the cash, where does it sit, and how do you cover the long-term-care risk that will eat through it?
If you take cash, where does it actually go? Split your after-tax proceeds between liquid (HYSA / Treasury / CD ~2.5%) and locked (MYGA ~5%) buckets. Visual cards + blended yield + CPA breakdown showing tax drag year-by-year.
GUL, S-GUL, IUL, 10-pay, Term, which fits at your age? Hockey-stick chart showing cost-of-insurance rising sharply past 60. When IUL is a mistake (68+). Comparison matrix with 6-policy types side-by-side.
How much tax-free LTC benefit does $100K actually buy? Solves for 4-Year and Unlimited Asset Care plans side-by-side based on age, sex, health, single-pay vs 10-pay, and optional inflation rider. Compares against the dollars you'd need parked in a MYGA to self-insure.
A CD pays interest you owe tax on every year, at full ordinary rates including the 13.3% California top. A MYGA defers all of that until withdrawal. See the actual dollar gap over 5 / 10 / 20 years on your specific marginal bracket.
If you take the cash and pay the tax, where does the rest sit? HYSA at ~2.5% or a Multi-Year Guaranteed Annuity at ~5%? A-rated carriers, state-guaranty backstop, 5-yr lock. Hans places these too.
70% of 65-year-olds need LTC. California memory care runs $8,500–$14,000/month and is rising 3-5%/yr. Two ways to fund it: SIS monthly payments cover the bill directly, OR a OneAmerica Asset Care policy delivers a 3-5× LTC pool (with a death benefit if you never need care). Plus the "stack both" case.
Federal LTCG brackets, NIIT 3.8%, CA marginal up to 13.3%, MHST 1% above $1M, all stacked. The actual effective rate on a CA real-estate or business sale, broken down line by line.
2026 IRMAA tiers, the 2-year MAGI lookback, and how a Year-1 cash sale punches you into a higher Part B/D premium for years. SIS structuring keeps you below the IRMAA cliffs.
LA Measure ULA mansion tax, SF transfer tax, Santa Monica Measure GS, Culver City, the hyper-local taxes on top of state + federal. Affects the seller, the deal, and the net.
Eight worked profiles: retiring rental owner, founder selling C-corp, ranch sale, primary-residence with §121, etc. Cash side, SIS side, decision logic, honest "neither" cases.
Eight situations most CPAs miss: primary residence over §121 cap, sale-to-kids deferral, inherited property + MYGA stack, dental-practice exit, partnership unwind. Where SIS does work, where it doesn't.
If you're on the buying side and the seller asked you to sign an SIS rider: every document, what it does, what it doesn't, and why it's NOT a 1031 exchange or a DST.
If your attorney structures a Charitable Remainder Trust, the heirs lose the corpus. Standard fix: an ILIT-owned guaranteed UL replaces the trust value tax-free outside the estate. The piece I handle.
The SIS uses an annuity, but it's NOT a SPIA. Period-certain only (no lifetime guarantee), taxed under §453 gross-profit ratio (LTCG rates) not §72 exclusion ratio (ordinary income). Visual breakdown of how a $200K annual SIS payment splits into basis return, §121-excluded gain, recognized gain, and imputed interest, plus a one-paragraph tour of every major annuity type (SPIA, DIA, MYGA, FIA, VA).
The entity that legally takes on the buyer's payment obligation isn't a mysterious third party, it's a wholly-owned subsidiary of the same Fortune 500 carrier writing your annuity. an A-rated Fortune 500 carrier Assignment Company and their assignment-company subsidiaries Why the structure exists (§453B, §130), how the corporate map looks, and how to verify any of them in 30 seconds on SEC/NAIC.
The most common SIS pushback: "If I'm OK getting paid over time, why bring an insurance carrier in?" 10 reasons it almost always goes wrong, buyer credit risk, divorce/death/bankruptcy interception, §453B prepayment trap, foreclosure costs, state-line enforcement issues, buyer-discount expectation. With the SIS contrast for each.
Asset protection from creditors (CCP §704.100), zero ongoing AUM fees (~$500K saved over 25 years), Social Security claiming flexibility, probate avoidance, NIIT cliff avoidance, IRMAA planning (both ways), state-tax arbitrage if you move to TX/NV/FL, DAF/charitable compatibility, no RMDs, and IRD/§691(c) inheritance treatment. The reasons sharp CPAs quietly keep recommending the structure once they understand it.
A plain-English guide for sellers: how a structured installment sale defers the tax when you sell a business, practice, or property — the math, the alternatives, and how to know if your deal fits.
Drop your info — instant PDF download + within 1 business day Hans will email a preliminary read on which structure fits your deal. No retainer. Carrier compensates the broker — not you.
📞 Hans Goldstein · 213-290-4977 · CA Insurance License #4322192 · Independent §453 specialist · Goldstein & Co. LLC
