There's a Pearson 33 in not horrible shape on St Thomas going for $4000 and like most boats in the sub $5K bracket it will need some work. I'm guessing not a lot...
Which is not to say you can't turn a good deal on a boat into a bloody money pit because I see it all the time. Folks try and turn a sows ear into a silk purse or forget the need/want equation and start replacing perfectly good systems with new more expensive stuff and that almost always turns into a monetary clusterfuck of epic proportions.
Not too long ago I read someone opining that it was impossible not to get screwed financially buying and rehabbing an old boat and then used an example of a guy who bought an old CAL for $10K, ripped out all of its systems (that were serviceable but not new or hip), and proceeded to replace them with the current flavor of the month "best" stuff and, well, apparently it got out of hand. As the writer pointed out this was proof positive that fixing up an old boat was always going to be a losing proposition.
What can I say... There are a lot of logic-deprived people in the world.
The thing is, the Pearson in question, even in perfect showroom condition, is, at best, going to be worth somewhere south of $20K so buying the boat for $4k and then pumping $60k into fixing it up might not exactly be a smart move. That said, I see folks doing the same exact thing just about every day and it's more than a little bit depressing.
Then again, with a little common sense, a passing knowledge of the need/want principle, and 50% of the purchase price set aside for needful repairs/improvements this particular Pearson 33 makes all kinds of sense...