My suggestion is to get a boat that (1) has a track record of doing the kind of things you want to do, (2) is well documented , (3) has a history of being reliable, (4) is inexpensive, (5) has good resale value, (6) Sail it for a while and then you can (a) sell it and move to the mountains and buy a farm or (b) get another boat suits you better or (c) just relax, hunker down and go or (d) ? .
Look at the pearson triton 28' (Carl Alberg design)
(1) James Baldwin: two circumnavigations
(2) James Baldwin and a Mainer that has a 10 STAR web site on a stem to stern total refit.
(3) generally considered to be simple/bullet proof
(4) $15,000 with diesel, new paint and sails seems to the rule
(5) It's not a Cape Dory or Pacific Seacraft but they do have a good name and a devoted following.
(6) Your call a or b or c or ?
James Baldwin's Website:
See his LINKS page for all the Triton info anyone could want....