Adventures in Boat Shopping

As some of you know I have been on the hunt for my own boat. I am looking for a 25 footer that sits on a trailer. Mainly so I don't need to pay winter storage fees but also as this is the land of 10,000 or so lakes, and there are a few I would like to visit and sail on. So I began looking intently a while back and I have had some interesting results. 

Where the hell is this "Buyer's Market"?. No idea where this glut of boats are but I sure as hell can't find them. Granted with my parameters it does limit my options a bit. Mainly to Catalina and O' Day 25's but, there is not many out there for sale. Or at least that I can find. I thought I found a couple of great prospects but, one got sold on me and another over in Wisconsin I thought we had a deal worked out but now I can't get the phone answered or a call back. 

Very frustrating as a lot of prospects are far away and I am not sure if I want to drive for 12 hours or a couple of days to find something that isn't up to snuff. Like one I found down south that come to find out has a mysterious leak and the trailer tires may not be OK. Wow, really? 

I understand that some boats may need some work but, let's not waste each others time here.  I am open to doing work, not that big of a deal but, I am not paying $4K - $5K for a project boat. Just not going to happen. I want to know for sure that the boat I end up getting is the right one for me and the sailing I want to do. I know how much I want to spend and I realize I have gear to buy too so that is part of my overall budget. Hoping to keep it all under, well under would be nice but this is a boat after all, $10K.

Guess I was a bit naive to think this would be easier than this. Just going to keep on plugging along and hoping that I can find something before there is too much snow on the ground around here.