Jeff, have you considered joining a yacht club? You will likely get more experience in bigger boats than by just taking lessons (and, many clubs have lessons available as well). I would also urge you to consider buying
a smaller, used monohull
that will sleep four in your second year and then get first-hand experience in navigation
(including bleeding your diesel), anchoring
, reefing, etc., etc. If you get a boat that is popular in your area, you should have little difficulty re-selling and the loss, if any, will be relatively minor in the overall scheme.
Understand that after only some sailing lessons
on the Canadian (Great?) Lakes, you will not be able to charter
CAT in the Caribbean without also taking on a skipper
. And I would imagine that you wouldn't (or at least you shouldn't) want to.
The bottom line, as I see it, is that you'll get the experience you need when you are your own skipper
, sail-trimmer and navigator. You will also get the chance to see if this is really the life for you and yours.