Toronto and Vancouver are great cities, but they are both getting very expensive. If I had a big pile of money, I would take Vancouver first, Toronto second. On a budget, I would take Montreal. The City has a great bike path system. It is very easy to get around without a car most of the year (take the bus in the winter). Plenty of affordable places to live. Lots of great festivals (Jazz, Comedy, Gran Prix, etc.). Close to good skiing that isn't so pricey, like Whistler has become. Can't beat Mount Royal for hill training. Great night life. Not too many tourists. Great restaurants.