I just published my sub-$10k boat expenses on two threads for my first three months in Florida. You can click on my username and look at threads I've posted in. It might be enlightening for you.
I sailed bigger keelboats for three years on trips up to two weeks long at a time, used to work house construction, and read extensively on how to inspect a boat. I inspected at least a dozen boats across florida and found only one that wasn't trash. Even so, I'm stuck without an engine
right now in Marathon.
This is not to discourage; I've had a fun time and met a lot of new sailing friends. But be aware that no matter what you buy or how much you put into it, sometimes you just draw the wrong card, and it's no one's fault. That's cruising. Still, it does change your cruising plans significantly!
I was feeling sort of down until I watched a few episodes of "untie the lines" on YouTube. That poor girl got her life put on hold by the boat she bought! I recommend you watch a few too.
I wish I could give you advice on where to find long-term crew opportunities. The thing about it is, I've been offered several, but only because the fact that I bought a boat and singlehanded it down here gave me credibility, and also gave me the opportunity to meet friends who needed help. When I was looking at crewing
opportunities online, I would likely never have gotten them. Moreover, they're mostly for deliveries, such as "help me cross the gulf stream
and then get the hell off my boat," not for "I welcome a complete stranger to liveaboard
my boat with me for the next few months while I cruise
paradise," unless, of course, you're young, attractive, of the appropriate sex, and don't mind being pawed by a degenerate forty years your senior!
It's a catch-22, you've got to own a boat you may not really want in order to sail on someone else's boat that you really do want
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