Rick-
I have been a lurker here for some time but after finding this post, I had to join sbc just to voice an opinion here. I love my boat. I love diving from my boat. I love sleeping on it up in the San Juans. I love fishing off of it on the Columbia River. Weirdest of all, I love working on it. It has inspired me to get back into diving.
It is everything that everyone has said stay away from. It's a 27 foot Bayliner from the mid eighties. It has a chevy 350 inboard and a volvo penta I/O. It's name is Midnight Star but maybe should be Just Barely. I can just barely dive off it- I wish it had more deck spece to suit up and a better swim platform. I can just barely tow it- it's the narrower 8 ft beam but you just wouldn't want to tow anything bigger. I can just barely stay on it for a week or so but it does have a galley, a head with a shower and a dedicated sleeping aft cabin. I can just barely afford it and frankly it's on the edge of what I want to pilot in close quarters.
I bought it salvage from an insurance co. after it sank-the one thing the other guys didn't mention is that most boats, other than the top brands mentioned, have fiberglass encapsolated(sp?) plywood for thier transoms(the big flat back end of the boat) and encapsolated wood for thier stringers. When left in the water for long periods, water finds it's way in and the wood rots- leaving the engine and outdrive mounted to a structure that is unstable and can move. Then when the boat hits something even as soft as a sandbar the outdrive pulls away from the transom and water comes pouring in. This is how I came to own my boat. Boats that spend most of thier lives on trailers don't usually have this problem unless they are left uncovered and turn into bathtubs. I've spent 2 years re-building it during the evenings when I could have been watching TV. I learned a whole lot along the way, and there were times when I just about gave up. I've got way less than your budget into it and I know every screw, nut and bolt and am confident that it is solid. I had a professional do the fiberglass and sent the heads off of the motor to a machine shop. Other than that I did all the work myself. The upolstery isn't perfect, there are scratches in the hull, there are some stains in the interior cushions. All that said it goes almost 40 mph and takes me and my wife to places I could never go without it. I don't take it much into the Ocean proper but there are hundreds if not thousands of miles of inland waters in the Puget Sound, the San Juans and on up through the Gulf islands into Canada. There is just something about being on my own boat late at night after an amazing dive, watching the stars, cooking something cozy and warm and then figuring out where we'll point it tomorrow. I've had a few "Oh- @#%!" moments as well but nothing a cool head can't get through.
As noted there will probably be many "projects" available because of the recent hurricanes. It's just a thought but I can personally recommend the elbow grease, tinkering and hard work methodology path to boat ownership. It takes some skill, some common sense but mostly just perserverence. There are a lot of on-line resources and many forums similar to this one where knowledgeable folks willingly help you out. Best of luck - Ace
"Future witty quote re:water and diving goes here"