The STR Deal Analyzer & Buying Guide

From the Wyo Stays team — a licensed Wyoming real estate brokerage. This is educational information to help you think clearly about a purchase, not financial or investment advice. Run any real deal past your own lender, CPA, and a licensed agent before you commit.

Buy the numbers, not the view

Every bad short-term rental purchase starts the same way: someone falls in love with a cabin, then reverse-engineers a story about how it'll pay for itself. The good ones start with a spreadsheet and let the property earn its way in.

This guide is that spreadsheet, in words. Work through it before you write an offer. (The gated Deal Analyzer worksheet and the interactive calculator on this page do the arithmetic for you.)

Step 1 — Estimate revenue honestly (not hopefully)

Revenue is ADR × occupancy × 365, but the honest version subtracts reality:

• ADR (average daily rate): what comparable Sheridan-area properties actually get — not the peak-week screenshot. Blend high season and shoulder.
• Occupancy: realistic annual occupancy for the sub-market and property type. A great property in Sheridan runs strong, but a rural cabin that only books in hunting season won't hold a citywide average.
• Seasonality: Sheridan is dramatic — WYO Rodeo week, summer, and hunting seasons carry the year. Model the low months at low numbers.

Gross revenue = blended ADR × realistic occupancy × 365. Be conservative here and everything downstream is trustworthy.

Step 2 — Subtract the real operating costs

New buyers routinely forget half of these. The honest operating stack:

• Cleaning & turnover (often passed to guests, but model it)
• Management (if you're not self-managing — and read the honest-math guide before you assume you will)
• Channel fees (unless you're driving direct — see the Direct-Booking Playbook)
• Utilities, internet, streaming, smart-home subscriptions
• Supplies & restocking / consumables
• Repairs & maintenance (budget a realistic annual figure, not zero)
• Insurance (commercial STR policy, not a homeowner's guess)
• Property taxes
• Lodging/sales tax remittance (a pass-through, but a compliance cost)
• Reserves / CapEx — the roof, HVAC, and hot tub that will eventually break. Set aside per booking. (There's a calculator for this.)

Net operating income (NOI) = gross revenue − operating costs (before your mortgage).

Step 3 — Layer in financing

• Down payment: STR/second-home and investment loans typically want more down than a primary residence.
• Rate: investment-property rates run higher than owner-occupied. DSCR loans (qualified on the property's cash flow rather than your personal income) are common for STRs — covered in the financing guide.
• Debt service: your monthly principal + interest.

Cash flow = NOI − annual debt service. If that's comfortably positive at conservative occupancy, you have a real deal.

Step 4 — The three numbers that tell the truth

1. Cash-on-cash return = annual pre-tax cash flow ÷ total cash invested (down payment + closing + furnishing + setup). This is the number that matters most — what your actual cash is earning.
2. Cap rate = NOI ÷ purchase price. Useful for comparing properties apples-to-apples, financing aside.
3. Break-even occupancy = the occupancy you need just to cover all costs + debt. The lower it is, the more margin of safety you have. If you break even at 35% and the market runs 70%, you can sleep at night.

The interactive Deal Analyzer on this page computes all three from your inputs.

The Wyoming buy-box

Across our portfolio, the properties that consistently perform share traits. Weight your search toward:

• Location that books year-round or has a strong seasonal engine — walkable downtown Sheridan, or scenic foothills (Story, Dayton, Bighorn access).
• A differentiator — a hot tub, a real view, a creek, character/uniqueness. "Nice but generic" competes on price; distinctive wins on ADR.
• 3–4 bedrooms — the group/family sweet spot (5+ earns more but is a bigger operation; studios have a lower ceiling).
• Clean zoning + no HOA STR ban — verify before you fall in love. This is the #1 deal-killer people discover too late.
• Manageable turnover — layout, hot-tub logistics, and access that a cleaner can flip reliably.
• Sane reserves — an older property can still be great; just budget its CapEx honestly.

Red flags that sink first deals

• Revenue projections built on peak week. If the pro-forma only works at 85% occupancy, it doesn't work.
• Ignoring setup cost. Furnishing a property to five-star standard is real money — put it in "total cash invested" or your cash-on-cash is fiction.
• Zoning/HOA assumptions. "Everyone around here Airbnbs" is not confirmation.
• No reserve line. The hot tub will need a pump. The furnace will age out.
• Underwriting to self-manage, then not. If your time can't actually cover it, you'll hire out — so underwrite the management fee from day one.
• Financing surprises. Second-home vs investment classification changes your rate and down payment; confirm with a lender first.

Your pre-offer checklist

1. ☐ Blended ADR & realistic occupancy from real comps (not peak week)
2. ☐ Full operating-cost stack modeled — including reserves
3. ☐ Financing terms confirmed with a lender (DSCR vs conventional)
4. ☐ Cash-on-cash, cap rate, and break-even occupancy calculated
5. ☐ Zoning + HOA/covenants confirmed to allow STR
6. ☐ Setup/furnishing cost in total cash invested
7. ☐ Deal still works at conservative occupancy
8. ☐ Exit in mind (what would this resell for — see the Scaling & Exit guides)

Want a second set of eyes — from people who actually run these?

We underwrite Sheridan-area STRs for a living and manage 95+ doors. Before you buy, we'll run your target property against our real portfolio data and tell you straight whether the numbers hold up.

→ Unlock the Deal Analyzer worksheet, run the calculator above, and → get a free buyer's revenue projection on a specific property.

Educational only — not financial, investment, or tax advice. Confirm every figure with your lender, CPA, and a licensed agent.