I've only lived in 3 major canadian cities.
Winnipeg(grew up there) - good: AMAZING skate scene with so many great parks, super cheap living costs, lots of good restaurants and a
coffee.
bad: murder capital of canada, most brutally cold winters ever, no freeways so getting around can sometimes be
frustrating.
Ottawa (lived for 2.5 years) - good: super scenic and beautiful, very safe, traffic jams are minimal, good people, pretty good food
bad: not one good coffee place in the whole city, 50% of the city wears suits everyday, not to many good
skateparks (although looks like a good one is just being built right now)
Toronto (been here for only 4 months) - good: mellow winters, insane amounts of good food/coffee, endless things to do. It's big.
bad: traffic jams always, even at 10pm on sunday, surprisingly few skateparks in the actual city,
everything is overpriced.
Final verdict: I like them all, but Ottawa takes the slight edge.