I think it is harder to build a team in Canada, you mostly have to do it through the draft.
Some Canadian cities are much harder (Winnipeg) to build in than others.
Anyone saying taxes, weather, and the media don't contribute has no clue.
Even if there are "world class cities" in Canada, there is a US city that offers the same or more, so there isn't an attractiveness to Toronto when New York and Chicago exist, Montreal and Vancouver are probably more unique and intriguing to some than Toronto.
The only thing they have going for them is players coming home.
When players get there, it depends on the person, but yes for some, no for others.
There is definitely more media pressure and some fans are insane, not sure this should dictate the play of some players, but I am sure it is easier to play for some with no pressure.
It's also the best place to play when you are winning.
Do you mind listing your life achievements so we can see if you are qualified to discuss succeeding under pressure?
You sound like a winner, so I am assuming the list is long.