@Marc ShinWe have a 2BR/1B and a 1BR/1B and are booked year round, even during the off-season.

I’m starting to trim back my portfolio a bit as I’m getting older and shifting strategies.

Overloading of circuits in older homes is a bigger issue.  

And with point 4 yes 18 months is a short window but much of my opinion is based on these being older, 70s and 80s homes (big assumption on my part). 

Distance makes investing more challenging, as does seasonal occupancy and governments which operate differently and/or are less stable than our own(though our own government has not been a paragon of stability lately.)By investing in the Caribbean, you’re adding those challenges plus you’re throwing in the occasional hurricane.  

I've found that some of my best deals have been off market with older investors that are wanting out of the game.

This makes it a great way to fill gaps and during the low season.

Do you foresee those older areas having high possibility of excellent appreciation over the next 5-15 years?

@Ryan Lee there are no seasoning loan programs out there.

If you ask your banker, your older parents or grandparents, realtor, financial manager etc. they will all say "of course buy your primary".