Starting with a big boat and/or one that "NEEDS WORK" is the downfall of many folks dreams. IF your DREAM is to SAIL then GO NOW on a smaller cheaper boat..... . MOST FIXUP PROJECTS FAIL! You might be the exception but why bother to find out the hard way if your goal is not to have a project but is to go SAILING! There are capable affordable boats that will get you started. Once you have crossed a pond and weathered a blow you, or you and your partner will be in a position to beat the odds and find one of those great ?big? great deal 'FIX-ER-UPPERs' and keep going in grand style. They are out there for sure. As a way to start out it is almost a sure fire prescription for failure. However, once you are 'ON THE WATER', and 'LIVING THE LIFESTYLE', you will be in the best possible position to find those great deals and also you will have the experiance to know which of the deals is the RIGHT ONE FOR YOU. They will nearly JUMP out at you and the folks you meet will tell you all about them time after time. Dashed dreams that can be bought for pennies on the dollar, blown op on the shores of 'Bit off More than I Could Chew'. The folks you meet in the anchorage know these things, NOT the folks on the street.
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....