Call me a cynic, but I really can't see the NHL going back to Winnipeg. Considering the latest "theme" of the NHL - expansion into ambivalent southern markets - I can hardly see Bettman/NHL turning around and giving Winnipeg the Jets back. They still own the Yotes, and will do everything in their power to keep them out of Winnipeg. I feel like True North is being used as leverage; I'm not sure of the actual legal issues involved in selling the club but I have a sneaking suspicion that the NHL will find a way to weasel out of True North getting the Jets if the Hulsizer deal falls through.
For all the people saying Hamilton... have you ever been there? Vile city; stayed there at a friend's place and it felt like the inner-city version of Trailer Park Boys. I live in nearby London, and its hard enough getting Knights fans (OHL) downtown to the arena to catch a game. There is no way an NHL team could work in this particular city due to all the constraints present (arena in horrible downtown location, no parking, incapable infrastructure). Too bad the prairies is pretty much a desolate wasteland; I'm sure there are a ton of hockey fans in Manitoba/Sask but I can't really see the Regina Rangers taking off.
Kitchener-Waterloo may work - two smaller mid-size cities right on a major transportation artery with a ton of space. The "Ottawa" Senators actually play in Kanata, with Scotiabank Place occupying a tract of land off the highway in buttfuck nowhere outside of the city. Likewise, having a team somewhere in SW Ont, preferably playing off the 401 would be marvelous. There is a shit-ton of the population clustered around that highway; guaranteed success. Yeah, it would dig into Buffalo/Toronto/Detroit, but a)Leafs fans are stupid to a fault and will always support the leafs, b) Detroit doesn't need any help with a fanbase and c) there's enough hockey fans and money in SW Ont to keep the Sabres and another team afloat.
Actually driving to Toronto, paying vastly inflated ticket prices thanks to MLSE to watch a mediocre team is keeping a ton of people away from Leaf's games. Considering the best go-to option for catching NHL is to cross the border and hit Detroit, putting another team in SW Ont is more viable than people think. There is actually a huge anti-Leafs/MLSE sentiment in the area - tons of local people identify with the Red Wings or Sabres. Consider you'd be drawing in fans from everywhere south of the GTA and north of Windsor - London, Hamilton, K/W alone could probably support a team.