I had a big, long post and accidentally hit something and lost it. Which is probably good, because I tend to ramble.
Here's the nutshell:
1) Get towing insurance; its cheaper than a single tow, and with a new boat, you may well need it;
2) Think carefully about how you expect to use the boat, and try it out to be sure it meets those needs (e.g., how many people will you typically sail with, and how will they fit in the cabin/cockpit?);
3) Think about where you're going to keep the boat, and make sure that the slip/marina is protected so you aren't blown about as you enter/exit;
4) Despite the low investment you're making, consider getting professional surveys of the engine and boat (a new engine is $2,000+, a boat survey is $350-400, and an engine survey will be a few hundred) AFTER you've done your initial review;
5) Depending on the boat you buy (I strongly encourage you to consider a Catalina 25 or 27), get a trailer;
6) Expect to put at least another $2000 into the boat; maybe not right away, but probably over the course of your first season.
I'm still a novice at all of this - I've bought 2 boats in 2 years. But the boats I've bought were in the same range as the ones you're buying, and I went aboard a TON of them (easily 10-15 the first time, and at least that many this time, too), and if you wind up in the NJ/Philly area, I'd be happy to go along with you to look at a boat or two as a second/third set of eyes.