Start simple. Get nuanced when you need to. Every calculator below uses honest math — different layers of detail for different situations.
If you take the cash, where does it sit — and how do you cover the long-term-care risk that will eat through it?
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.
