I have certainly criticized the current FO (and I think it's more than just Chiarelli that deserves blame) but they deserve more rope than this. If they make a few shrewd moves to clear cap space / bad contracts and some of their minor league talent makes the jump they should have better depth again and the team should be basically fine. They still have a top goalie, top center and two good defensemen (one who should keep improving in the near future) under control for a while and they will be out of the "bad" contracts soon. I don't love the Krejci or Seidenberg deals but DK is still a good player and if Seidenberg never returns to form you can deal with one bad contract. So all told that's a very nice core just as it was last year, and with ELCs contributing you can sign a couple key UFAs for depth and be in good shape.
But it's certainly a key moment for the team. If guys like Koko, Spooner, Morrow, or Pastrnak don't develop, or if they extend someone like Lucic long-term for too much money, they could get stuck in medocrity (I don't think they'd ever bottom out with a very high pick, either, as Rask, Bergeron, Hamilton, Chara are enough to keep that from happening). And Chia has to pick the right guys to sign or trade for, and results are mixed there.