Scott I have a Sovereign 23, 5'7" headroom, fixed keel, trailerable and not too ugly a coachroof or excessive windage. The interior layout could definitely be improved on, but all in all it shows that the size boat you are describing is possible. I think one or two people could spend some extended time aboard, my wife and I spent two weeks in the Keys aboard a few years ago and we're still married!
Sailson