I too am in the research phase of my first boat, and I too plan on living aboard in Toronto, sailing the Great Lakes and eventually going offshore and ... well, pretty much wherever. I am hoping to buy the boat in about two years time.
So far, I have narrowed it down to the following
Pacific Seacraft Dana 24
Pacific Seacraft Flicka 20
Bayfield 29 (although I find it too beamy)
J.J. Taylor 26
I believe that there is no right or wrong boat, it is all up to the individual - besides, if we all had the same boat, things would be boring.
Good luck in your plans and maybe one day, we'll be neighbours!
p.s. Have you ever read the book "Twenty Small Sailboats To Take You Anywhere" by John Vigor? I recommend it highly. Nautical Mind carries it and so many more books.