Don't get attached to any one boat or buy under time pressure. Watch the Annapolis/B-more/eastern shore craigslists for a month and you will see tons of good simple boats in you price range. Read the sticky thread about doing your own survey and go visit a couple likely boats - you will quickly see what looks well cared-for, as well as learn how to dig in the corners (how do the keelbolts look? Are the backings of the chainplates accessible? Bottom of bulkheads or portlights show signs of water?) Capt. Aaron's advice to keep it real simple is dead-on. Oh, and run the motor and sail before you buy.
Doing this summer as a club member and crewing on as many different kinds of boats as possible, then buying in the fall is a good idea.
What about my answer to the original question - "Talk me into it..."? No need. Sail once. If you're hooked, you're hooked