I was first considering a larger boat and going further, but upon the advice of my buddy Stephane, who is currently circumnavigating on a contessa 26, i've decided to scale back a bit. He first did some southern cruising on a trimaran before buying his contessa.
I've bought a small boat, will do the repairs and outfitting myself, therein learning the ins and outs of the boat, and then finally take this little boat on some extended cruises on the great lakes, home to Nova Scotia, and eventually south. After this experience, I may have my fill, but if not I'll be much more prepared to buy larger (or not) and go further.
Without getting ahead of myself, as life has a tendency to alter plans suddenly, I'm honestly very much looking forward to working on the boat and getting my hands dirty.
Good luck deciding! I hope I'll see you out there on the lake one day.