Comparing Winnipeg to other cities, in terms of amusement parks, high end retail stores, etc is NOT the reason players don't want to play for Winnipeg. It's two main things, and to a lesser extent weather:
1. Living under a microscope. Winnipeg, Edmonton, Calgary, and Ottawa will all instantly recognize most NHL players. Not much privacy for an NHL player. You may not like what I have to say, but I somewhat agree with Kane. He was constantly under scrutiny from the media and fans for his actions outside the rink, even though at the end of the day, they were not that bad. Kane was immature, and it could be argued he was a problem child, but he has a valid point.
2. History/success. A big factor for many who want to come to play here. The Jets/thrashers have not made the playoffs since 2007, and even though we are improving, players are not convinced the Jets are a legitimate contender. If the Jets made the playoffs for 3 years in a row, this will change, considering True North has proven to be an above average ownership group. This is why players choose to play for Pittsburgh, and Detroit.
3. Weather. This is not as big of a problem as one would think. A lot of players live away from Winnipeg during the off season, and even if they do live here, many of the Jets 1.0 would comment on how it's an underrated city, and a great place to raise a family. Summers here are great, as there are a ton of festivals, lakes within an hour, and nice weather for 5 months a year.