The STR Feasibility Checklist

The eight factors

1. 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. 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. 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. 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. 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. 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. 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. 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.

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.