Thanks for all the tips guys, I seem to be getting a better idea of what sort of boat to get. I want to avoid the trap of just getting a bigger boat, I still think something around 27 is my best bet - small enough to singlehand whenever I want, large enough to weekend with a few friends.
I don't need the "best" boat around, but don't want the "worst" - I don't care about luxury, just decent quality - so I guess "mid-range" boats are my target.
C&C 27 looks pretty good so far - found one for $11,000 in maine, take a look:
http://maine.craigslist.org/boa/263180610.html
Seems to be alright... any thoughts?