I've been here for almost 10 months and quite frankly don't think I'll ever leave. It's a fantastic city and Canada is a great place to live. It isn't just an accident that it usually places in the top three for places to live.
Commuting can be bad, if you can use transit do so. I'm lucky, my commute is less than a 30 minute drive.
It's more expensive than Fort Collins CO, or similar towns in the US (mid size) but it's one of the largest cities in NA. You can buy a decent house for $450K, less if you look around (I'm in the West Bloor neighborhood and paid far less than that for a detached bungalow). Can you do that in New York, Chicago, LA, or Boston? If you compare it to other cities it's size, it's pretty affordable.
Coming here from the US was simple for me. I got a job offer and applied for a NAFTA work visa. If your profession is on the list, it's dead easy. I'm now in the process of applying for my landed card (similar to a green card).
The weather is great. I love the winter, as I am an avid X-country skier. Toronto motorsports park is 90 minutes away. You can do a lapping day there (9am till dusk) for $150 bucks. A steal. Food and nightlife is also great.
I still want to have a meet up for a beer with the GRM GTA folks. MW, put me on the list for a ride in the firetruck.