I remember hearing that there weren't many but there definitely were a handful of shops ready to go on day one.
For all intents and purposes, it's basically legal in Toronto. The police here barely can be bothered to go after violent crime half the time, let alone worry about pot unless you're growing industrial quantities or doing something exceptionally stupid. They have enough to worry about with the thousands of crack and heroin dealers. People stroll down the main streets all the time openly smoking joints, just today I was walking back from lunch to work behind a woman who was hauling away on her vaporizer on Yonge St. right in front of a cop.
My dealer is part of a group of about 5-8 people who bike around town all day, 7 days a week. You call them up and say where you are and within 15 minutes they'll meet you anywhere within about a 400 square block area. It's faster and more reliable than ordering a pizza. There's nothing shady about it either - we'll go around a corner if there's a cop standing right there but otherwise it's an open exchange on the sidewalk on Queen St, just the same as if I was buying hot dogs.
Society survives. The most obnoxious thing I've ever seen someone doing with weed is rolling a joint in the back seat of a busy streetcar. On the other hand, people drink to the point of blackouts, shoot heroin, and smoke crack in the back of the streetcars, so nobody gives a shit about weed here.
The only real difference if they legalize it in Canada (for downtown Toronto, anyways) will be that my buddy will go out of business, and I'll go to the corner store instead.