Sunday I helped a young friend of ours bring his recently acquired San Juan 24 to Shilshole Bay from Everett, WA, a pleasant five hours on the water. He bought this little boat, his first, for less than the cost of one month's moorage.
The boat is no wreck. Quite the contrary, although she has been somewhat neglected for the past couple of years. The boat has no engine but a small outboard borrowed from my friend's Dad solved that, pushing the boat at hull speed through the still waters of Puget Sound.
The standing rigging has been recently replaced, the bottom seems reasonably clean, the bilge dry and the sails, including the roller furling genoa, in decent shape. She even has a working VHF, depth sounder, compass, and a new knot meter which the previous owner said he never finished hooking up in addition to a manual Whale Gusher bilge pump, water tank, holding tank and head. The seller threw in two inflatable PFDs, still in the packages and two anchors with rodes. The boat is set up for racing with six winches and color coded lines led to the cockpit through labeled cam-cleats. She would be perfect for single handed sailing.
We had a little wind for a couple of hours and set the sails. She sails very well. A great little boat, ready to sail for practically nothing. She needs a good cleaning more than anything. After that, a weekend with a little sandpaper, paint and varnish will turn her into a nice little yacht.
I was there when the deal was struck so I know that this is not just one of those yacht club bar stories.
My point in all this is to demonstrate that good, well equipped boats can be found for very little money. I also know of a Vega 27 that was purchased for $500. I have seen larger boats abandoned in boatyards to be eventually cut up for scrap. Some, certainly, were not worth the cost of saving but others could have been had for a few hundred or a couple of thousand bucks. You just have to keep your eyes peeled, have cash in hand and be in the right place at the right time.
If circumstances allow I would recommend getting a job at a boatyard or chandlery to put yourself in a position to find the deals. If you are retired, spend time at the marinas and boatyards in your area. (Showing up at 5:00 with a twelve pack is a great way to make friends among the yard workers who can give you the hot tips)