This is 100% the problem. NHL executives are over valuing their product. There is a small dedicated fan base which will pay a small premium to watch all NHL, or every game of their favorite NHL team, and that's it. This isn't the NFL or college football we are talking about here.
The answer isn't in jacking up the price. The answer lies in getting the most volume, that's eyeballs watching your broadcast. Even if they had to lower the price to something like $5 a month they should do it. Hey if Disney can to it, the NHL can. Here's another thought. They might want to archive and make available past Stanley Cup Finals or great playoff rounds. I know in the dog days of summer I might get a kick out of watching Bobby Orr, or Wayne Gretzky in the playoffs one more time, but at my leisure and when I decide I want to watch it.
I am a Pac-12 fan. The Pac-12 Network is run the same way as the stupid LA and NY RSN's. One of the things I look for when I sign up for a service is the Pac-12 Network and other outlets such as FS1 that carry Pac-12 games. The people that run leagues and conferences better figure it out, and soon. They might want to try starting their own app and not being part of a bundle. I would pay maybe $10 a month for an ala carte niche product like the NHL or the Pac-12. Just don't gouge me on the price though, and there better not be any blackouts for any reason.