It did cross my mind a few times after I went out and some family have done it and there are ties with other family. I don't think I'd be able to due to health insurance and such as I have too many medical problems.
The winters can be harsh though they are more equipped for it out there and there is a whole underground system in Toronto!
http://www.toronto.ca/path/
I'd say you would need to drive and have access to a vehicle as round where I was things seems to revolve around people being able to drive. Lots of drive through Tim Horton's coffee though :)
Have you been there before?