Hi Susan --
My window is closer to yours -- my older son just went to college, my younger is a junior in high school. With my business, I can be anywhere, so I'm starting to think seriously about where to go. But as for a boat, all the suggestions you've gotten sound like terrific boats. You could also check out John Kretchmer's Used Boat Guide (Sheridan House, 2002, ISBN 1-57409-150-6) for some good ratings -- he has several idices that are good to know (safety, market value, durability, etc). While all the suggestions are good, I don't know that you can get most of them in your price range. No matter how good the boat's condition is, you should keep a sizeable reserve for inevitable maintenance expenses -- so I would figure a maximum you can afford, and shoot for at most 70% of that.No matter how great the boat is, it's useless if you can't afford a new alternator or get the roller fixed. I realize this sounds obvious, but it's easy to start thinking that extra 4 or 5 grand when you are looking at boats. I deal in violins, and I see it happen all the time -- my most difficult job is trying to keep clients from spending too much upfront.
I got a Pearson 30 this past spring up in Boston, and sailed it down to Greenwich, where I keep it. A great boat;fast and responsive, but good in heavy weather. The latter I discovered when I got caught in a ferocious gale the last day -- the worst weather I've ever been in, and I've sailed all over for 40 years now. I like the size -- plenty of room down below, but not so far to the foredeck that you can't get back to the cockpit in a hurry.
Prioritize what matters, and you will be able to get something at a surprisingly good price. Engine, prop, decks, hull,
rigging -- they are what count, but price is driven by appearance; wood and so on. Whatever you think is important, that's fine -- but make a list before you even start looking. It will help keep you grounded when you see the gorgeous teak and chart table etc.
Anyway -- good luck!! And welcome back to the water -- Jim