Investor Resource
Hospitality Investment Due-Diligence Checklist
Every item below has saved an investor money — or every item skipped has cost one. Work through these six phases before you close on any hotel, motel, or vacation rental in Orlando. Print this page and check each box as you go.
Strategy & Pre-Offer
- Define your strategy: value-add, stabilized, STR, or NNN retail
- Set budget, target cap rate, and hold period
- Confirm financing pre-qualification (DSCR, conventional, SBA, or bridge)
- Identify target submarket and acceptable distance to attractions
- Decide self-manage vs. professional management before you buy
Legality & Zoning (STR — Do This First)
- Confirm exact jurisdiction — city vs. unincorporated county (property appraiser site)
- Verify parcel-level STR zoning (Osceola GIS map / county zoning lookup)
- Confirm STR license availability — call the county/city department directly
- Request and read the full HOA CC&Rs — look for rental/transient occupancy rules
- Get written confirmation from the HOA manager that STR is permitted
- Check for minimum-stay requirements (HOA may impose even where county doesn't)
- Verify owner-occupancy is NOT required for your jurisdiction
Financial Due Diligence
- Request trailing 12-month (T-12) actual P&L — not projections
- Verify T-12 against tax returns and bank statements
- Analyze occupancy and ADR/nightly rate trends (3 years if available)
- Model NOI at conservative occupancy (70%), not the OM assumption
- Calculate DSCR at your actual loan terms — confirm ≥ 1.25x
- Calculate cash-on-cash and IRR at conservative and realistic cases
- For STR: review 12–24 months of Airbnb/VRBO booking and revenue history
- Confirm what taxes the platform remits vs. what you must file (TDT)
Physical Inspection
- Inspect HVAC systems (hotel HVAC replacement = $2–4K/room if failing)
- Inspect roof, plumbing, and electrical
- Check fire suppression and life-safety systems (egress, detectors, pool barriers)
- Inspect elevators if applicable
- Assess renovation needs and budget ($12–18K/room for value-add motels)
- For STR: confirm furnishing condition and what conveys with the sale
- Order a Phase 1 Environmental Site Assessment
Franchise & Brand (Hotels)
- Review the franchise agreement — remaining term and renewal options
- Identify any required Property Improvement Plan (PIP) and its cost
- Negotiate PIP costs into the purchase price
- Confirm you will be approved as a franchisee (transfer process)
- Understand franchise fees and their impact on NOI (4–7% of revenue)
Financing & Close
- Match loan type to asset (DSCR for STR, conventional/CMBS for hotels, SBA for owner-op)
- Confirm down payment (25–35% typical) and reserves
- Lock rate and confirm DSCR clears the lender's threshold
- Secure property and liability insurance (and STR-specific coverage)
- Register with Florida DOR (sales tax) and county tax collector (TDT)
- Confirm exit strategy: hold, refinance, or sell — at which cap rate?
The #1 hospitality investing mistake:skipping Phase 2 (legality & zoning) for STR purchases. A great financial model is worthless if the property can't legally operate as a short-term rental. Verify jurisdiction, parcel zoning, license availability, AND HOA permission — all four — before you fall in love with the numbers.
Tools to Work Through Each Phase
Vacation Rental Calculator
Model NOI, cap rate, DSCR, and cash-on-cash (Phase 3)
Open →STR Zoning Guide
Verify legality by jurisdiction (Phase 2)
Open →STR-Approved Communities
Community-level STR status (Phase 2)
Open →Hospitality Financing Guide
Match loan type to asset (Phase 6)
Open →Florida Vacation Rental Tax Guide
Tax registration and remittance (Phase 6)
Open →Deal Analyzer
Full institutional underwriting (Phase 3)
Open →Want us to run this checklist on a specific property?
We verify zoning, financials, and HOA compliance for properties our clients are considering — before they make an offer. It's the fastest way to avoid an expensive mistake.