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. MetLife Assignment Company (MACI), Pacific Life & Annuity Services, Berkshire Hathaway Assignment Company, USAA Assignment Corporation, etc. 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.
