I'd love to help, but I don't know where to start. Have you gotten
far enough along the path to know: Where you planning to sail and in
what seasons? How much money are you willing to spend? How rough you
intend to live? I suppose if you want to sail you will be well served
getting some sailing lessons and I'd go the keel boat route if you are
feeling as old as I do these days. However, I would no obsess about
it. Some of the technically best sailors I know are horrible
cruisers. A good attitude and a boat you are confident in can take
you a long way.

-- Tom.