Won't losing show that this Team is regressing and is further away from a cup than they were the past 3 years?
I don't see how that could be viewed positively.
A best of five playoff series is essentially a coin toss, so I don't see it as any kind of definitive evidence that the team is regressing, especially after a 3+ month hiatus from real, game scenario hockey.
Even if it were a regression, that's pretty normal. No NHL team progresses in a linear fashion. Some seasons you take a little step back, and then you take a little step forward, and keep going up and down. Look at teams like the Capitals, Lightning, or Bruins, who have been in the mix for the last decade or so, but have all even missed the playoffs at least once in the same time, but then retooled to be a bit stronger. At a certain level you can't get "better" every season - you just do your best to stay good. Good enough to make the playoffs, which are essentially a slightly weighted crapshoot every season, based more on hot-sticks, streaky goaltending, and good luck than the actual on-ice talent of each team involved in a series. Ideally, you stay good for 25+ seasons like Detroit, and maybe win 4-5 championships in that time.
The positive of losing the series is that it doubles our odds of getting something good (12.5% of lottery win vs 6.5% chance of Stanley Cup win), and that thing we might win (Lafreniere) is an actual asset, not just a trophy memorializing a tournament victory. Of course, the Stanley Cup carries a lot more significance, but not technical value that can be accrued towards winning more games & Stanley Cups in the future.