I agree that a 30 footer can be found for $5000 but it's going to be old and in rough shape and while sailing the Bahamas isn't bluewater sailing, there's still a lot of open water between islands and I don't think I'd want to be out in that open water in a $5000 derelick. Remember, you get what you pay for and your life will depend on the seaworthiness of your boat.
I think your painting with too broad a brush.
I paid under $2000 for a 32' 30 year old boat and it came w/ a kubota 4cyl. w/ less than 200hrs. all bronze through hulls. swageless rigging etc etc. there are alot of boats around and alot of people who want to part w/ them .
As for the distances from fla to the Bahamas, I think bimini is 48 miles away !! an overnight sail.
Also to say an inexpensive neglected boat is not or would not be "sea worthy" is too general a statement .
I could sight dozens of examples of folks sailing far on less and w/ less.
I'm exhausted with the repeated mantra of and from folks about how difficult and dangerous sailing is and how one needs a certain boat and equipment. It just isn't so, please quit perpetuating this mistruth. how many accounts of completey inexperienced sailors making long trips and extended cruises successfully will it take to show sailing is just not that rixky or complex?
And the "classes " and "courses" are SOOOOOooooooooooooooooooooooooo lame. just read a little and take an interest in it and you will learn /know all that you can without actually doing, after that doing will expose the rest.
I've sailed the hell out of my $2000 dollar boat and she has many more miles left in her.
just do it, do it.