I do think there is trouble brewing with the team with the departures of D & Z, which is coming sooner than most hope. Regardless of when they stop playing, they are in decline now and likely subject to potential injury concerns. It's a fact of life and comes with age. There are very, very few exceptions to that. Lidstrom was one of the exceptions, his game didn't decline too much and he wasn't susceptible to injury too much either....mostly because of the style of game he played (wasn't centred around speed or physical play). You don't have that same scenario with Z & D.
That said, not sure I'd start thinking there is a paralell with the Dead Wings era because of the era we are in now, it's easier to rebuild. Teams are much more competitive, the worst teams are not that much worse than the best teams. From a points perspective, some of that is artificial because of the points system, but some of it is just pure factual due to the spreading around of talent. Teams can't load up on all the superstars anymore due to the cap. Of course, you could look at it being increasingly difficult to make the playoffs as well due to the competitive nature of the league as well.