Professional Short-Term Profit Analysis

[Mike Bauldree]

I've spent the last year doing deep research on Caribbean and international STR markets — USVI, Aruba, Dominican Republic, Bahamas, Barbados — evaluating whether these markets actually pencil out for US investors versus domestic coastal alternatives.

One thing I kept running into: there's almost no serious underwriting tooling for international STR deals. AirDNA doesn't cover these markets well. Mashvisor doesn't touch them. Most investors are building their own messy spreadsheets and hoping the numbers work out.

So I built something: https://caribbeanstr.com/

It's an AI-powered STR underwriting tool that takes a property and spits out:

- Three-scenario pro forma (upside/base/downside)

- Full expense model including hurricane insurance, HOA, management, CapEx

- Market-specific risk flags (weather, regulation, legal, saturation)

- Tax and legal notes (1031 eligibility, FBAR triggers, foreign ownership)

- Comparable deal benchmarks for that market

- Plain-English verdict: buy, conditional, or pass