We only do it occasionally because usually the Hard Money Lenders we work with will provide me 75% of the ARV anyway. 

I have someone who occasionally works for me that has extenuating circumstances.

Occasionally an igniter goes, the TPR fails, the drain valve goes, or the thermal coupler.

Occasionally see places in Weatherford, Azle, and Bridgeport. 

I now have the card where I can use it occasionally and it will add to the amount of available credit.

In short, I'll never do it again unless the relationship began as a business relationship that later evolved into a friendship and even then I'd be very selective.In my experience, over time, lines got blurred and our relationship evolved to a point where every conversation mentioned the business in some capacity.

To maximize return requires occasionally extracting value.  

We would use it 1 week a year (like we do now) so the 3K we'd normally pay would be used by the condo and the occasional get away during off-season.

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.  

Yes, you should ask about wind insurance as we do get wind damage occasionally from hurricanes although it is far milder than the coastal areas.