A lot of you are calling for a dramatic increase in the # of outdoor games. Having a home-and-home outdoor series, for example.
But the NHL is rightly concerned about diluting the Winter Classic brand, and rightly so. At the end of the day an outdoor game is just a gimmick. It's taking standard old NHL hockey and putting it in a different environment. And once you put the gimmick aside, the hockey itself isn't as good. The ice tends to be poor unless the weather is just perfect. Because games are played in baseball or football fields the in-person fans sit way too far away from the ice.
I would love to see Winnipeg get a Heritage Classic. I think it will happen in the fairly short term - the ones in Edmonton and Calgary were big hits, but there are few other locations which could host an outdoor game right now (stadiums in Toronto, Vancouver and Montreal all have roofs, and the other alternatives have fewer seats than the existing arenas). So Winnipeg is the only other option.
When Landsdowne is rebuilt maybe Ottawa will get a Heritage classic, but that's about the only other option.
But don't expect it to be any more than it is - an occasional once-per-year gimmick game.