Back to the thing about the Pens, they are a small market team who is able to spend like a big market team because of their sustained success over the last decade. They 100% need to keep it up because as soon as they have an extended rebuild, they're toast. There is no money in the Pittsburgh market for a bad team.
The only thing that saved them the last time around was being gifted Crosby and Malkin.
I don't think the NHL will let a franchise with 5 cups go belly up, so something will be done if it ever comes to it, but the decline of the Steel industry in the US (and manufacturing in general) has made Pittsburgh a less than sustainable market from a money perspective. (unless there is perpetual success)
There are other markets that have been hit hard by this, namely Detroit, but the population of the Detroit metro area is about double that of Pittsburgh, and the team has fans with much deeper roots than Pittsburgh, being an O6 team and all.
Admittedly in my life there has never been a perpetually bad Red Wings team, so we may learn more about this in the coming years.