Run your rentals before they run you. A career-transition planner for STR hosts asking the real question: when can I quit? Calculates your quit date — optimistic and conservative — based on your portfolio’s actual numbers. Excel. This is not a hype workbook. It will not tell you to quit tomorrow. It will tell you, based on your W2, your portfolio’s current Schedule E numbers, your savings rate, and your household expenses, how many years and months until the math actually works. The answer is rarely what you hoped. It is usually further out than the gurus claim and closer than you fear. The spread between optimistic and conservative is the conversation you have been avoiding with your partner. WHAT’S INCLUDED — LITE ($27 ETSY) Excel workbook (3 tabs): - Start — THE quit date. Optimistic and conservative dates side by side. The spread between them. Four critical numbers: properties needed, cash needed at quit, healthcare bridge cost, projected Y1-after-quit net. - Current State — W2 income, STR portfolio (gross + Schedule E line 26 net), household expenses, liquid runway, partner W2, employer benefits value (401k match, health insurance, life, disability). - Target State — replacement income, buffer multiple (default 1.5×), reserve target, properties needed at current per-property economics. Lite calculates years-to-quit. Full adds the acquisition schedule, healthcare bridge math, partner risk-share, and the printable Conversation Doc. WHAT’S INCLUDED — FULL ($47 OWN-SITE) All 3 Lite tabs, plus: - Acquisition Schedule — year-by-year property adds with cash deployment. Y1 net per added property defaults to 65 percent of stabilized (because Year 1 is harder than the brochure). - Risk Plan — healthcare bridge math (COBRA at 102 percent of premium for 18 months, then ACA), insurance gap, partner risk-share slider 1 to 5 driving the conservative scenario. - Quit Date Calculator — toggle Optimistic vs Conservative. Different occupancy assumptions, different acquisition pace, different appreciation, different buffer multiples. - Conversation Doc — one-page printable for the kitchen table conversation. Quit dates, four critical numbers, three biggest swing factors, action plan, partner sign-off lines.
Related
- Break-even Occupancy Calculator
- Cost-to-Launch Calculator
- Year-2 Operator Bundle
- Schedule C Tax Prep Workbook (Active STR)
- Rental Arbitrage Analyzer
What's inside
- W2 earners with 1 to 5 STR properties asking when they can quit
- The analytical partner who needs the spreadsheet to confirm or kill the dream
- Pre-purchase operators validating that the path is actually realistic before buying
- Anyone whose partner has asked "so when CAN you quit?" and they did not have an answer
- Anyone looking for a "quit your job in 90 days" hype workbook. We do not sell that.
- Households relying on W2 spousal income that has not been factored in. The workbook handles dual-W2 cleanly; single-income paths work but are not deeply modeled.
- International hosts. US healthcare and tax assumptions only.
Get the workbook
Format: Excel .xlsx + how-to PDF. Excel 2016+, Excel 365, Google Sheets compatible. Instant download after checkout. 14-day refund, no questions. Lifetime updates within v1.