I agree with your general assessment, except I don't know what kind of "talent evaluation" would have lead to this team having more elite talent on the team right now. If Holland got what he wanted we'd have Babcock coaching a team with Suter and Stamkos on it, imo that would have been a pretty good team.
Show me the receipts. It's already been disproven many times that Tatar's numbers were due to Datsyuk/Z. He produced with everyone. Tatar-Sheahan-Jurco was the first "kid line" and they did great. They were even deployed like a 2nd line for some periods of time when we had injuries and whatnot, so it's hard to argue that they only produced because of easy matchups.
Nyquist is producing decent numbers now but even so his numbers are clearly hurt from poor coaching (non-existant PP) and Nyquist said the coaching staff was on him about shooting the puck more which lead to him scoring 28 goals. Now with Blashill he has become a 10-20 goal scorer.
There is a talent defiency but the same players who looked talented playing tough matchups 2-3 years ago even when Dats and Z were injured now look completely lost and untalented playing 5-on-4 hockey against Arizona. Something is wrong, clearly.
Talent evaluation includes both judging what players will be good, and what players are no longer good (or good enough, as the case may be).
Since 2012, this franchise's run of actually contending for a championship was over. At that point, talent evaluation should have included trying to trade assets while they still had value, not continuing to stockpile average players and hand out long-term deals with no movement clauses.
Fan reaction be damned: the proactive path would have included things like trading Datsyuk once you knew he was flaky about staying here a week after signing a new contract.
But Holland - whether through his own hubris, an edict from ownership, or a combination thereof - just doesn't know when to let go. So here we are, sliding towards limbo, with little to no assets to help build it back up.
And had they added both Suter and Stamkos - however unlikely that possibility - they're still a 2nd or 3rd round exit. Now had they made those moves, and had more success because of it, maybe they also make another move or two, and they win another Cup, or at least make the Finals again. But that's a whole lot of ifs. What DID happen is that, in each scenario, they had a #1 target that, in hindsight, was never likely to come here, and they had no great Plan B for the chance that they struck out.