I've been thinking about this throughout this year's playoffs. I have always dismissed the conspiracy theorists around here as just being tin foil hat nutjobs, but I don't think that they are completely off-base.
Let me say first and foremost that I do not believe that there is a blatant conspiracy or intent by the league to selectively eliminate certain teams from the playoffs, or help other teams to get deeper in than they normally would.
What I do believe is that Gary Bettman, and I assume those under him, places a strong emphasis on the expansion and extension of the league into new markets as well as an increase in popularity in already-established markets. Everything that he does is to this end. I have no doubt that people in the upper echelons of the NHL casually discuss how it will help the league for Sidney Crosby to win cups (being the next Wayne Gretzky and all) to help with universal league appeal, and how it will help the league for small and non-traditional market teams to achieve success in the post season. That's why the salary cap was such a sticking point in the negotiations that culminated in the league losing a season due to a lockout. Bettman would rather not play an entire season of hockey than allow the league to continue with no salary cap, because that's how important league parity is to him. Parity means that small market teams will start to experience more success. (Ironic that the last team to hoist the Cup before the lockout was Tampa.)
I think that it is an attitude that pervades the league's offices, not some sort of unwritten policy. I don't think that Bettman or Colin Campbell calls up Terry Gregson and tells him that his officials need to make sure that the Sharks beat the Wings or that the Penguins win the Stanley Cup. I have little doubt that people in the league feel that the Wings going deep into the playoffs every year is detrimental to the NHL because it is keeping other teams out, thereby preventing the growth of those teams' fan bases. Again, no one tells anyone that the Wings need to get jobbed, but I think that there is a pervasive attitude in the league that leads to negative feelings towards Detroit.
Ultimately, I think that the League's front office places more emphasis on marketing and monetary expansion through the development of under-performing markets and lucrative television contracts (that really have yet to materialize) than they do on officiating and making sure that games are run properly. It's possible that young refs aren't as experienced as they should be or aren't trained as much as they should be. Not because the league is purposefully trying to screw over certain teams, but because their priorities are elsewhere. Instead of worrying about putting out a quality product that will appeal first and foremost to hockey enthusiasts, they are spending their time trying to appeal to the mouth-breathing masses. It's the same reason that reality television dominates the airwaves instead of higher-quality programming. In terms of fans, the league is going for quantity, not quality.
Anyway, those are my feelings on the matter. I think that as long as Bettman or someone with his mindset is running the league, it is never going to be as good as it could or should be. The recent news about the Coyotes and what happened in Winnipeg further supports that. It doesn't make sense that cities like Quebec City, Winnipeg, Hartford, and Minneapolis lose NHL franchises while warm-weather cities that don't traditionally care about hockey gain franchises. These cities all ostensibly have bandwagon fans that jump ship as soon as their team starts sucking, while the cities that lost their teams are left to wonder if they will ever have an NHL team again. Again, this is bad for hockey as a whole, but it's where Bettman's priorities lie.
I will agree that they seem to be aiming for quantity rather than quality, and that is, in my opinion, a detriment to the game and the league in the long run.
I think what Bettman must realize is that people prefer originality to commercialism, especially in a day and age where we are constantly bombarded with redundant ads and marketing gimmicks. Sure, clever marketing schemes and changing the game drastically may get people's attention at first, but people might eventually see the NHL for what it has become, something that is unoriginal rather than unique. In doing so, they run the risk of alienating traditional fans and boring new ones into extinction, similar to what happened with NASCAR.
They seem so caught up in marketing the game for what it could be rather than what it already is. How does Bettman expect anyone to respect the game when he clearly does not? That is simple psychology right there.