People conflate country club with lazy. The Wings are overly loyal, but the guys they're overly loyal to are the guys who are easy to like from an organizational standpoint.
The warriors who bust their ass even when they don't have it anymore. I mean, it's a problem that they need to address, but I really don't think the Wings locker room is a "show up, cash check, live forever" location. It's really one where they fell in love with guys with intangibles and valued intangibles and character over talent and skill.
Hank could conceivably coast and just ride out his deal as a 3rd line guy... but he takes the mantle of leader seriously. Kronner and Ericsson could hang them up now and nobody would fault them... but they want to play so they grit it out on bodies that have betrayed them.
They got blinded a little bit because the guys they used to have at the top of the roster were lunch pail dudes who had Cadillac skills. Pavs, Z, Yzerman, Lidstrom, Chelios, Shanny, etc. They were hard edge dudes even when they couldn't play physical. They killed themselves at the rink to stay at the top. The Wings went too far in trying to keep guys with that work ethic but have not been able to find guys with the skill to back the ethic up.
The Wings were good for decades because their skill guys were tough mother****ers. Now, their skill guys are small and neutralized pretty easily and the size they have just isn't that great at hockey.