Re: A bluewater live-aboard for under $20k
First of all, I would suggest that there almost no such thing as a solid 'blue water cruiser' for less that $20,000 ready to go. At best you are looking at compromises.
Boats like the Alberg 30 (I raced offshore on one of these), Triton (I have a lot of hours on these) and Vanguard (my family owned one of these) were mediocre boats offshore, when they were new and they are now nearing (and most cases passing) 50 years old. These are tired old boats with designs that never were very good offshore. And yes, I know that people have taken them offshore and survived. I did not say that they can't be taken offshore, I just said they never were very good for that purpose.
Of the boats mentioned above, the Tartan 30 would certainly be my first choice. You should be able find a clean one in your price range, and would be a good choice to cruise the Bahamas and Carribean. But even if you found a really clean one around $10K there is a whole range of things that you would need to do to go cruising on one. You would want to add more water and fuel tankage, heavy air sails, good ground tackle and ground tackle handling gear, a good way to deal with the 'dinghy question', if they are not there-add self seteering gear, teathers and strong points, backing plates to heavier loaded items, and so on. Even doing your own work, you can quickly burn up $10K.
I would set it up with hank-on 110 jib that can be reefed and with a downhaul to strike it from the cockpit.
It may be old, and pressing your budget, but at least with the Tartan 30, you would end up with a boat that sails well.
Very close behind the Tartan 30 is a bit of a rare bird, the 1960's era Galaxy 32 (AKA as the Metal Mast 32 and Paceship 32). These were amazingly advanced boats for their day. Well built and sailed extremely well. If they were more common, they would be number 1 on my list.
Other favorites of mine are the the Bristol 33/34. I saw one go for around $15K last year and that would have made a great platform for some serious cruising. The Pearson 10M (33) were a nice design but not as robust as some of these. One of the least known really neat boats is the mid-1970's era, Ray Richards designed Cheoy Lee 32 sloop/cutter. All you just need to do is find one with an aluminum spar and the teak decks removed. Another design which is often overlooked is the Pearson 323.
If you have your heart set on going 'old school' I like C&C Corvette, followed by the Bristol 29/30 (not to be mistaken for the 29.9), (1960's era) Morgan 34, the Tartan 27 and then there is the Seawind (mk1) if going painfully slow isn't too painful.
Anyway, these are a few quick suggestions but they might move you in a direction that has not been mentioned......
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay and part-time purveyor of marine supplies