The biggest mistakes first-time STR investors make happen before they own the property — they happen at the verification stage. Here’s the checklist.
Pre-offer verification (do all 12)
- Town-level STR legality — written confirmation, not just a Google search
- Zoning district restrictions — some towns allow STRs only in specific zones
- HOA or condo association rules — many ban STRs outright; some require board approval
- Permit timeline and fees — factor into your launch date
- Realistic revenue projection — not the seller’s number, not the AirDNA number, but a comp-based analysis
- Comp set quality — direct competitors with similar bedroom count, location, amenities, and seasonality
- Operating expense reality — cleaning, supplies, software, utilities, internet, maintenance reserve
- Mortgage product fit — STR-friendly lenders exist (DSCR loans); not all conventional mortgages allow STR use
- STR-specific insurance availability — some carriers won’t cover certain markets
- Cash flow at 60% occupancy — your underwriting should not require 90% occupancy to break even
- Tax strategy fit — does the 7-Day Rule apply, and can you materially participate?
- Exit options — can the property convert to MTR or LTR if STR rules change?
The post-close 30 days are everything
Most owners lose 60-90 days of revenue because they don’t have a launch plan. Listing copy, professional photos, strategic pricing setup, guest comms automation, cleaning SOP, and insurance/permits all need to be live on Day 1. The properties that hit five-star revenue in their first season are the ones that operationalize from Day 1.
How we help
Our signature property performance analysis covers items 1-12 of this checklist before you write the offer. After close, our Do It With You and Do For You tiers cover the launch playbook so Day 1 is a five-star opening, not a soft launch. Request an analysis.