I bought my first boat last summer - a Santana 21
I found it listed on Craigslist for $2000
It had a 7.5HP Chrysler outboard and the sails were in "decent" shape and it was "ready to sail"
The boat was down in Corpus Christi - About 4 hour drive away - so i called the guy and asked what was his lowest bottom dollar number he would reasonably take for the boat. He said $800 so I said I'll be there tomorrow
Great deal IMO - BUT:
When I bought the boat I had to put two new rims on the trailer (about $150 total) before I could even tow it home.
Once I got it home I found a brand new (still in the bag from the sail maker) main sail and some other goodies..
I had replace the chain plates as they were completely rotton from corrosion and completely replace the standing rigging. All the running rigging was 3 strand rope/wire so I replaced all of the halyards and I've added a few other goodies to the boat.
Anyways, My point of this story is - Be ready to put some money in to what ever you buy - and haggle haggle haggle...
All said and done I've spent about 2500 on this boat + marina fees to keep it at the marina (stepping a mast every time you want to take the boat out becomes a real pain in the butt real fast)
Everything I've bought for this boat I've gotten for at least 10-15% cheaper because I was willing to ask "whats the best price you can give me on ...."
Hopefully I can get a new spinnaker and genoa for this boat on the cheap too.. I'll find out later this week i suppose