Investment insights for the Caribbean & coast
Market comparisons, tax incentives, and underwriting strategy for short-term rental investors.
The 14-Day Rule and Other STR Tax Mistakes First-Time Investors Make
The IRS uses the number '14 days' in two completely different STR tax rules that are easy to conflate — and confusing them can cost you either a clean tax-free income stream or your ability to deduct losses against other income.
Read article →The Outer Banks: The Risk vs. Reward of STR Investment
The Outer Banks is the most established STR market in North Carolina — and also one of the most exposed to hurricane, insurance, and erosion risk. Here's how to weigh both sides honestly.
Read article →Realistic Cap Rate for a Carolina Beach STR
Cap rate headlines for coastal NC properties get thrown around loosely. Here's how to calculate a realistic number for a Carolina Beach STR, and what's actually driving it.
Read article →Cash-on-Cash Return vs. Cap Rate: Which Number Should You Actually Trust?
Two investors can look at the same STR listing and walk away with completely different numbers in their head — because they're answering two different questions. Here's what each metric actually tells you, and when to lean on which one.
Read article →CONFOTUR Explained: The Tax Break Dominican Republic STR Investors Are Missing
CONFOTUR can exempt a Dominican Republic short-term rental from property tax, transfer tax, and import duties for up to 15 years. Here's how it actually works and who qualifies.
Read article →Aruba vs. Dominican Republic: Where Should You Buy an STR in 2026?
Both are Caribbean STR powerhouses, but they reward very different investment strategies. Here's how the two markets actually compare on revenue, regulation, and risk.
Read article →