30-Second Cash vs SIS Answer

How much will your California sale
actually cost you?

Five inputs. One answer. Find out in 30 seconds whether a Structured Installment Sale would keep more money in your pocket than just selling for cash.

What's SIS? Structured Installment Sale. Sell once, get paid in monthly checks for 5–40 years from an A-rated insurance carrier. IRS taxes each check as it arrives, not the whole sale up front. Smaller checks = lower tax bracket = more kept.

Your numbers

All five fields matter. Income is the big one, it tells us how badly the tax stack hits you.

Gross contract price.
Purchase price + improvements
If yes, applies §121 exclusion ($250K single / $500K MFJ)
This is the most important field. Your existing income determines whether the cash sale punches you into top federal brackets (37% LTCG + NIIT + MHST cliff). Higher income = SIS saves more. Be honest, be a little high if anything.
5 yrs15203040 yrs
Advanced inputs (depreciation, prior 1031, city tax), only if relevant
Rental/commercial only. §1250 at 25% fed + CA marginal.
If you 1031'd in, the carried-over basis from the original property.
Need more knobs? The advanced calculator has all the dials: city/county tax, HYSA/MYGA blend, SIS yield slider, life expectancy, devil's-advocate scenarios, etc.
Your answer
Same sale. Same 4% yield. Different tax exit. Here’s where you land after 20 years.
Take the cash
—
Pay $— in tax up front. Reinvest what’s left at 4%.
Structure it (SIS)
—
Smaller tax bills spread over 20 years. Each payment also grows at 4%.
SIS keeps you ahead by
—
SIS pays you ~—/yr after tax for 20 years, smaller tax bracket each year, all of it compounding.
Where the win comes from
Pure tax savings
If neither side earned a dime of interest.
+—
smaller brackets, year after year
+ realistic 4% growth
When your money keeps working.
+—
tax savings + compounding
SIS wins both ways. Even with zero growth, you keep more on tax alone. Add realistic 4% and the gap widens by —, that's compounding on a larger pre-tax base, because SIS hasn't handed Uncle Sam his cut up front.
—
For CPAs & sophisticated sellers
Want every dial? Open the Advanced Calculator.
§1202 QSBS · §1245 recapture · IRMAA tiers · CA MHST · non-resident WH · cap-loss carry · COLA · deferred-start · income variation · §691 IRD · buyer concession · GUL overlay · year-by-year schedule · IRR · break-even yield · color-coded math breakdown · share scenario URL.
Open Pro →
Assumptions, conservative on purpose
Want every dial? The advanced calculator has carrier-yield slider, HYSA/MYGA blend, devil’s-advocate comparison, life expectancy, etc.
Disclaimer:Illustrative projection only. Actual returns vary. Carrier credit rates change. Tax law changes. Annuity guarantees subject to claims-paying ability of issuing carrier. Not tax, legal, investment, or accounting advice. Consult your CPA before acting on any number on this page.

Is this real? Walk through your specific numbers with Hans.

30-minute call. No pitch. Bring your CPA. Either SIS fits your sale or it doesn't, you'll know in 10 minutes.

213-414-2808, Talk to Hans
Show me the math, tax breakdown line by line

Cash sale, Year-1 tax

Federal LTCG—
NIIT (3.8%)—
California tax—
CA MHST (over $1M)—
Total tax—
Net cash kept—

SIS — 20-yr amortizing annuity @ 4%

Annual carrier payment—
Gain recognized per year—
Tax each year (LTCG + interest + CA)—
Net each year (after tax)—
Total tax over 20 yrs—
Value at year 20 (net + 4% reinvest)—

Assumptions:Apples-to-apples 4%/yr yield on BOTH sides over the term. Cash net is reinvested at 4% taxed yearly as ordinary income (your marginal rate); SIS uses 4% carrier credit on the principal balance (amortizing annuity), with each year’s after-tax payment also reinvested at 4% taxed-as-earned. 2026 federal + California LTCG + NIIT + MHST brackets applied. No city tax, no IRMAA modeled, no carve-out (100% structured), real carrier rates run 4.5–5%. Advanced calculator exposes every variable.

Next step · for sellers age 55+

This calc shows ONE term. The optimizer tries every term, and tells you which one wins.

If you have a pre-tax IRA/401k, the SIS unlocks a Roth conversion window in the years before RMDs kick in. The optimizer factors in your age, IRA balance, Social Security, and IRMAA cliffs, then ranks every SIS term 5-40 yrs and picks your sweet spot.

Run the full optimizer with your sale →
Take this with you

Save this analysis · Email it to yourself or your CPA

Save a beautiful PDF for your records, or have Hans send it to you (or directly to your CPA) from [email protected] with the full math breakdown and IRS citations.

PDF saves locally. Email comes from [email protected] with the full report inline.
Four tools, one math engine

Each calculator answers a different question. Pick the one that fits yours.

30-sec gut check
Quick Calculator
"Should I even consider SIS?"
4 inputs only, sale, basis, income, term. One number out. Bracket-math expander shows the work.
Skip if: you need multi-year planning, QSBS/§1245, or retirement modeling.
Open Quick →
Tax-forensic · 5 min
Tax-Detail Calculator
"What's my exact year-1 tax bill?"
Every factor a CPA cares about: §1202 QSBS · §1245 · §453A · §199A QBI · city transfer tax · §121 · prior 1031 carry. Color-coded live math breakdown, every formula visible.
Skip if: you want lifetime planning or bucket allocation.
Open Tax-Detail →
Bucket strategy · 5-8 min
Cash-Flow Planner
"How do I split the proceeds?"
Allocates proceeds across liquid buckets (HYSA + MYGA) and SIS. Models deferred SIS start age, multi-phase income (working → retired), apples-to-apples after-tax yield, inflation-adjusted IRR.
Skip if: you just want the tax answer or you're age 55+ and need RMD/Roth modeling (use Lifetime).
Open Cash-Flow Planner →
Lifetime plan · 5-10 min
Lifetime Optimizer
"What's my whole retirement plan?"
Optimizes SIS term 5-40 yrs across your full retirement. Models RMDs (age 73/75), Roth conversion ladder, SS taxation (0/50/85%), IRMAA 2-yr lookback, bracket inflation. Year-by-year ledger with IRS citations on every formula.
Skip if: you don't have a pre-tax IRA/401k or you just want the year-1 number.
Open Lifetime Optimizer →
Honest order: If you're new here, start with Quick. If your CPA needs to verify the math, send them Tax-Detail. If you're planning how to actually deploy the proceeds, use Cash-Flow Planner. If you're age 55+ with a pre-tax IRA, the Lifetime Optimizer is the strongest tool. All four show the math.
What this calc handles: Federal LTCG (IRC §1(h)) · CA progressive (CA R&TC §17041) · NIIT 3.8% (IRC §1411) · §121 home exclusion · §1250 depreciation recapture · CA MHST.
What needs a 20-min consult: QSBS founder stock (§1202) · §453A interest on big deals (>$5M) · SF/LA city transfer tax · Roth conversion ladder during your pre-RMD years · RMD/IRMAA interaction · IRD treatment at death · multi-state if you move out of CA · K-1 lumpy income · trust structures. If any apply to you, that's the conversation. 213-414-2808