The floor in our apartment was unevenlike a funhouse at a carnival, and there were soft spots where ourfeet would sink in.

I would recommend finding a reputable company like First American that also maintains insurance on themselves in case an employee runs off to the Caribbean or something with the cash.

In a catastrophic event- most likely a hurricane or flood from storm surge given that it's in the Caribbean, the Strata maintains enough insurance to rebuild pretty much entirely, this is part of the Strata fee, which is quite reasonable given the rental rate. 

It has a reputed medical school, it is a popular Caribbean vacation spot too.

This may be a long shot but anyone have an idea on if this arrangement exists in the Caribbean and standard pricing structure?

I've not studied the trend information closely, but with the growth of Nashville and the reduction in international/Caribbean travel this should continue to be an 'in demand" destination.

Realize you want to stay in the neighborhood, but now is a great time to move into the Caribbean islands after the hurricanes. 

I’m from a little island called Puerto Rico in the Caribbean.

I currently have a few properties in the Caribbean with low debt to equity ratios. 

I currently live in Jamaica and am an active real estate agent and consultant in the Caribbean and US.