Gas vs. Diesel (are we crazy)?
I agree, If I had my choice I would also try to look for a deisel. I think you can find one in your price range. Try looking at a Watkins 27 you should be able to get one in around your price range. Obviously they will come in all sorts of condition, but most if not all are with in board deisel. They don''t have the teak and holley floors like some, but they are a solid and sturdy boat. And they are not the best/fastest boats out there, but with a shoal draft of 3''11" they are good for your type of crusing. I was through some heavy seas in one and I always felt safe. Think of it as a poor mans Island Packet 27'' I would look for one with the bigger 15HP yanmars (2QM15) that came with some of them.
Look here http://watkins.realshell.com/