I'm a bit late to the conversation, but you might want to take a look at a Cal-24. Classic Lapworth keelboat design, fast, capable (one even circumnavigated...look for info on Robin Lee Graham and Dove) and there are a fair amount of them out there that have been properly maintained and are in your price range when available. They have a plywood deck core, so any signs of a significant lack of maintenance rules out many. We had a Cal 27-T/2 which sailed siglehanded like a big fast racing dinghy and I even knew an owner that trailed his C-27 all over the Midwest, but I wouldn't recomend that.