Toronto: (haven't lived there in a while, but...)
pros: Friendly people - even members of other tribes
Clean streets
Excellent public transportation system (technically feasible to get by w/o car)
Many parks/playgrounds (every few blocks)
Low crime rate
Wide streets (room for parking
and! driving
Lots of kosher food / restaurants / great bakeries
Variety of schools/yeshivos for the whole spectrum
Variety of sports teams, miscellany of museums incl. Hockey Hall of Fame
World's only yeshiva for the deaf
Eruv covering most of Jewishly inhabited areas (one of the best there is, halachically)
Though there is a measure of autonomy to all shuls/rabbis, there is a central authority as every Rabbi/community concedes to a single Rabbi who is recognized by all as (unofficial) chief Rabbi
There are tuition breaks (w/o being on WIC
)
Snow removal is swift, efficient and includes sidewalks
Growing young communities in multiple areas
free health care and monthly child allowance
driveways, garages and yards
Jewish employers who hire in
AND outside job opportunities have gotten better AFAIK
Kalman's kishke
Cons:Higher taxes (someone's gotta pay for insurance)
tough job market
Really long and really cold winters
Snow, usually lots of it
Did I mention the winters?
Price premium on many kosher products (import expenses)
While remaining low, crime has increased in some areas, mostly due to low income projects being built
My parents live there (okay, okay, not really relevant to most of you)
Gas prices are higher than USA
Housing is not cheap
Cons really boil down to expenses and winters. Personally, I would easily move there if not for the winters. It really has big city benefits and small town attitude.