I don't even think they failed to be honest. Zach Hyman and Warren Foegele are productive players now and they probably will be for the next several seasons. There are definitely some busts, but the free agent market is stock full of them every year.And they failed. The answer is to do it right, not throw all your hopes on the shoulders of an aging, oft-injured and extremely expensive goalie five years removed from elite performance.
Skinner looks ready to play a regular role as back up or even 1B now. Seems likely we'll start seeing guys like Holloway, Broberg, Samorukov and Lavoie vie for NHL jobs by next season with Bourgault coming up after, so 3-4 years seems excessively pessimistic. Also none of those guys are going to be asked to make "a huge impact" they just need to be better depth options than the worn-out husks we're throwing out in the bottom six now.
The problem with the roster right now is primarily the injury/COVID stuff, but it's also how guys are being deployed. Losing Larsson hurt and Tippett hasn't figured out how to work his roster without him as a fallback.
I'd like to see the depth chart I posted earlier. And I'd like to see Holland go out and grab a big bodied forward like Nick Paul or Zemgus Girgensons to add to the bottom six depth and spend the majority of the deadline assets on a LD that can do some of what Larsson did. Neither breaks the bank and neither casts a cloud over the team long-term.
This roster as is will make the playoffs this year. Plenty of divisional games left and a number of guys who historically thrive in the later stages of a season.