willyknuckle I am sure that the san juans could keep you busy for some time, make your focus smaller to begin with so that you can get a better grasp on what exactly you want to look for in a larger boat as well as the bare nessisities you will need.As far as ssmall boats go anyone who sailed around the world in a boat under 26 feet bought it brand new. Cal also made the 29-9 which a gentleman just recently sailed around the world in I believe it was a 60s model. Check out ready for sea by Tor Pinney. It has a great bare minimum list.I know for a fact you can buy a cal 34 for $10,000 bucks and some would dare to say take it anywhere.
i'll check that cal 34 out. thanks!