Admiral Beez
Superstar
After immigrating to Canada as a 5 year old in 1976, I grew up in Mississauga - living in the area of Derry Rd and Winston Churchill Blvd, until I moved to the Toronto Beach(es) area at 17 years old in the late 1980s.However, it seems some people are eager to recommend places like Cabbagetown, without mentioning any of the caveats, like what has been mentioned in this thread.
I can tell you, Meadow'jail as we called that area of Mississauga was, for me at least, a bed of idle friends drinking, smoking pot, getting arrested, petty crimes, poor performance at school, absent parents, etc. Moving to the Beach(es) where I met some great, academically-focused friends at Malvern Collegiate and turned my life around, and now living in Cabbagetown I am surrounded by neighbours and home owners I really like, and with whom I share much of the same sense of professional middle class home and community pride. Meanwhile, that area of Mississauga where I once lived is a dump of falling apart 1970s houses and infrastructure.
I'm much happier raising my daughters in Cabbagetown than I'd ever be in Mississauga, Brampton, etc. Some of the better suburbs such as Milton and Oakville by the waterfront are good, and friends in Georgetown love it there, but I'm a downtown Toronto guy by heart. I lived in Fredericton, NB for three years and while we had a nice house and such, I really missed the urban life.