Y'know, I failed to mention this, but you might consider looking at a Beech Musketeer. They're a little odd-looking compared to sleeker airplanes, but they're roomy. I flew one a few weeks ago and thoroughly enjoyed it. Feels and handles a bit like a truck, but in a good way, if that makes any sense.
I had lunch with the owner yesterday, as a matter of fact. He's had the plane a few years, has put about 350 or so hours on it. Never had an annual run him more than $1800 (including repairs.) He's got the 200hp Lycoming in it. Cruises at a decent clip, seems to be built like a tank and the fuel burn isn't awful.
They're not as pretty as some other airplanes, and thus they are well within your price range as far as I've been able to tell.