Winnipeg?!, umm, I know they had their team,, but,, nope,, I don't think it would be a good idea to go back there,, and don't get me started with another team in toronto's area,, let's think this through correctly,,, they have, toronto, buffalo, detroit, all of them within 4 hour drive or so,,, adding another team in that area would be REALLY stupid. Also,, I'll be honest and say, NO to a team in Quebec either,, I don't think it would be that profitable.
Also,, expansion in Europe as you've said would be very impractical,, tho,, a stanley cup final featuring the top team of the NHL vs the russian one,, ,,, OMG', no, the stanley cup should always be the biggest honnor in the NHL,,, if you wanna make a new tourney like the best 6 team competing for a new title, that might be worth thinking about (not sure it's worth to try tho) but not share the stanley cup with another league...