Comparing Bettman to Eagleson is disingenuous. Eagleson preyed on a venerable band of mostly uneducated players. Bettman represents 30 mostly very well informed, mostly very educated owners. Bettman is a sly man who knows how to operate in an unpredicatable/chaotic mess to take the heat while still helping the overall goal. Eagleson was a conman who was able to con a few players into agreeing to terms to lead the rest of the players, mostly uneducated players who were conditioned to do as they were told.
Say what you want about Bettman, but the guy is a very good at succeeding at his bosses goals (ie increasing franchise values). But I think you give far too much credit in the decision making process. We all know Calgary is not going anywhere. He is just supporting an owner (his bosses) with the talk right now. He is the figurehead, but everyone knows that the owners pull the strings on him.
Calgary is a mess. Bettman right now is running the Flames party line of that you will lose the team if you don't acquiesce. Whether that's true or not is hard to see as of now.
As for Winnipeg, I think we still have some time. I fully admit I thought when we built MTS centre at 15K we were done with the NHL. We've gone a bit above that with renovations and apparently 15Kish has been ok so I will support that. The rink is still only 17 years old with massive renovations over past 5 years. For a new rink who knows what could happen? While I do think Chipman and co should be thinking about it, its still at least 10-15 years in the future. Our very VERY high average ticket price will support us for a while yet.
I don't like the Headingly to Kanata/Glendale/Sunrise comparisons. For an accurate representation of that we'd have to build a rink 30 mins north of Selkirk for it to make sense. I don't know how much people know about where those rinks are, but for example of Glendale it's like a 45min+ drive from downtown Phoenix, nevermind the 1hour+ drive it is from Scotsdale/Mesa/Tempe/Gilbert who the people are. Even in Winnipeg no one is driving to say almost Portage La Prairie for a Tuesday night tilt against the Coyotes or Panthers.