Well since you are willing to drive 3 hours and spend $2K... here is a West Wight Potter (very well respected boat!!!!) on eBay. These are truly several steps up from what you have looked at so far.
West Wright Potter 19' with Aluminum trailer
http://www.ebay.com/itm/West-Wright...item462aee4bfb&item=301367970811&pt=Sailboats
and it comes with an outboard motor too... and a full compliment of sails. If you figure you won't need to buy an outboard, you could kick your bid up to $2500 and this would be a steal if you win the bid.
This one also looks very sharp
http://www.ebay.com/itm/A-very-rare...item3f3fbd0fd2&item=271652294610&pt=Sailboats
Remember one thing when buying a used sailboat.... you are actually paying for the trailer, sails and outboard. Think of the boat as free. All the mildew and bad paint, chipped fiberglass etc. can be fixed cheap. A new outboard motor is easily $2000 and a new set of sails also $2000 and a new trailer... also $2000.... so don't get hypnotized by the romance of the boat. You can make her your own with a little fiberglass, paint and a few hand tools once your bring her home on the
road worthy trailer....