I got lucky and developed a very good friendship here at CF. My wife and I drove from Texas
to meet up with him, and met his wife. We spent a week staying with them on their boat. A few months later, he asked if I wanted to crew for them from Florida
. I jumped on it, and had a great time. I was lucky.
The thought of putting a total stranger on my boat isn't very appealing to me. You only have their word as to their experience. Maybe they sneak a little dope aboard.....and customs
stops you for an inspection
(and you get your boat impounded)? Ok, maybe a little drastic, but who knows. And you are right, "compatibility" is a big deal. I worry that finding the right person(s) to sail with on the internet
isn't going to be without a few disappointments.
Where in the Caribbean
is the new boat? Maybe make some actual sailing friends there, and do some sailing together. Finding someone with some real experience wouldn't be a bad idea, considering your own experience?
Best of luck to you, but be careful.