This -
Plus stuff like this with essentially zero evidence to back it up:
I could and have discussed each of the "7 Contracts of hell" (Helm, Abby, Howard, Glenny, Nielsen, Dekeyser, Ericsson) at length. I understand why they're disliked but I personally wouldn't feel a lot better about our rebuild if we had just thrown 7 terrible young prospects into those roles instead or filled those spots with cap dumps or UFA garbage bin players. I wouldn't mind paying 10 million to Abby if he got to play with Zadina and Hughes on ELC contracts and the team did great. Basically I don't give a sh*t if a 20 year old is vastly underpaid and a 33 year old is overpaid as long as the team is good. And I don't give a sh*t if no one is overpaid if the team still sucks. I sure as hell think it's a lot easier to get rid of a bad contract than it is to fill a roster with quality people and players if you let everyone walk as soon as they demand more money (aka, turning into Ottawa).
In vacuum, you may be right. Real world, a lot more comes into play. You've got a 1st year coach that you prevented from talking to other NHL teams on the promise that he'd be the Wings next coach. Team is in a playoff position... and you sell? Ouch.
Larkin and Mrazek carry you towards the playoffs... and you sell, effectively killing their season? Ouch.
Your biggest star and audience draw contemplates leaving for Russia while you hope you can entice him to stay one more year... and you sweep the legs out from a playoff team? Yep, no way Holland gets blamed for Datsyuk choosing to leave after that.
Etc.
It's just not normal. Even as mediocre as the team looked that year, if you don't take the chance you'll never know. You could have spent the next decade wondering if Z and Dats didn't have one last run in them in 2016...