In response to OP: Seto could only produce with top line minutes on Jumbo's wing. Most legit NHL players could too. Seto can't even stay in the league now. DW got assets for a player on the decline. Heatley was NOT a top 6 forward by the end of his time as a shark. he was a 3rd line PP specialist and DW did absolutely the right thing getting his contract off the books when he did because we needed the cap space to re-sign Couture and Pavs. Same with Clowe and Murray who lost too much of a step and couldn't keep up. Look at both of them now. Don't ignore that both were already doing poorly in their last days in teal. Handzus also mercifully shipped for picks. My point here is DW always managed to get something for players that are on their way to obsolescence. That counts for something. I agree that DW however often misdiagnoses the team's needs.
Hertl's downturn is worth serious consideration. Some of that is due to reduced ice time and not playing with top linemates, but he's still down. This merits further consideration. Right now Nieto has the exact same amount of pts and games played as he did last season. I don't know why anyone expected 60pt seasons from him, he's just not that player. If you're currently disappointed with Nieto your expectations were unrealistic.
Coyle may still have some untapped potential, but Tommy Wingels has produced more. Coyle wouldn't save this team and would likely be playing 3rd line minutes over who?
You made no mention of defense and that's where the Sharks have taken a larger step back. Average goaltending behind worse D compounds the problem. The PK is also back in the toilet (LR reduced coaching role related?). The outlook for the next few years isn't great short of something drastic happening, but hopefully a high draft in a good class this year can help refill the prospect pool. We're not in Edmonton, we'll be alright. Hopefully we get treated to an underdog playoff run or two in the meantime.
As far as playoff failures go I think a lot of that is on TMac and the core players. TMac is definitely a smart player but it's also very clearly his way or the highway. His stubbornness, goalie grinding, and inability to adapt to the opposition in a series hurts. As for the core Joe is an amazing player and clear HHoF'er, but he's predictable as can be and the PP going 0-16 last year was telling. One critical flaw of this team has always been in the postseason that if you shut Joe down, you shut the PP down. If the PP dies and the PK stinks as it often does, you lose the special teams battle every series.