Streamlined Stays

Deal Score

Score your STR deal.

Answer eight questions about the deal you are weighing and get an instant go, lean, or no-go read, with the specific risks flagged.

This tool is a structural self-assessment only. It is not financial advice and not a substitute for a professional Feasibility Screen. Your answers produce a directional read - 'worth looking at more carefully' or 'several flags worth understanding first.' It does not predict revenue, occupancy, or returns. No two properties or markets are identical.

0 of 8 answered

  1. Have you confirmed that short-term rentals are legally permitted at this property's address - including any permit, registration, or owner-occupancy requirements?

    Local STR regulations vary dramatically by city, county, and HOA. A property in a jurisdiction that restricts or prohibits STRs cannot operate regardless of its other qualities. This is a go/no-go input, not a minor detail.

  2. Does the market have demand in at least 8–9 months of the year, or do you have a plan for a highly seasonal property (e.g., a shoulder-season use case, a long-term rental as fallback)?

    A 3-month peak market compresses revenue into a short window and raises the risk of failing to cover fixed costs in the off-season. Seasonality is not disqualifying, but it needs a deliberate plan.

  3. Have you looked at the active listings in this market and confirmed the property can be differentiated - by design, amenities, location, or experience - from what already exists?

    Saturation without differentiation leads to price competition and lower occupancy. A commodity listing in a crowded market is a materially different risk than a distinct property in a less-supplied segment.

  4. Have you stress-tested the numbers at 55–65% occupancy (not best-case assumptions) and confirmed the property can service its debt and operating costs at that level?

    STR revenue is variable. Planning around peak-year projections without a conservative floor is how buyers end up underwater. The question is not whether it can make money at 80% occupancy - it's whether it survives a slow stretch.

  5. Do you have a realistic estimate of the all-in setup cost (furniture, photography, supplies, platform onboarding, any required repairs), and does that fit within your capital plan?

    Setup costs for an STR are consistently underestimated. A property that pencils out at a given purchase price may not when $25,000–$60,000 in furnishing and prep costs are added. This affects your actual return basis.

  6. Is the property in a condition where it can be operational within your target timeline, or have you accounted for renovation time and cost in your underwriting?

    A property that needs 6 months of work before it can generate revenue is a different investment than one that can be listed in 30 days. Carrying costs during build-out affect the economics meaningfully.

  7. Do you have a clear, realistic plan for day-to-day operations - cleaning coordination, maintenance response, guest communication, and pricing management - that does not rely on 'figuring it out later'?

    STR operations are active work. Properties without a defined operating model before launch consistently underperform those that launch with a plan. Operator quality is a direct revenue driver.

  8. Have you confirmed your financing approach - including whether your lender allows STR use - and factored STR insurance costs into your operating budget?

    Some conventional loans prohibit STR use. STR-specific insurance typically costs more than standard homeowner's insurance. Both affect your real cost structure and should be confirmed before closing, not after.

Prefer to work through it on paper? Get the printable checklist