I think much this goes back to the fans and the "Minnesota Nice" mentality. Around here the ownership and management generally get long leashes. If you're the owner, all you need is the willingness to spend money, and then unless you're completely incompetent at hiring management (Glen Taylor), you're pretty safe even with years of mediocrity. And if you're the GM, as long as team's performance isn't a pure dumpster fire, you're given years to implement your "plan", and then we're very generous with accepting excuses. Generally we do demand that the players play hard, so that alone can drag so-so teams in to the playoffs. But once we're there, the talent level isn't close to moving on.
You're seeing this with Leipold and Guerin. Leipold has always spent to the cap, but even though we lag in other fan-centered areas of the organization (in-arena production, media, etc.), there's been little criticism of him. And with Guerin, this was the 6th season and will be the 6th offseason for him. It's been nothing more than further first round exits, and we're burning the prime, cheaper years of Kaprizov and a few others while we languish. But criticism of him has been spotty because of the Parise and Suter contract resolution, even though it was Guerin's choice to do it the way he did. He was not forced into a scenario where we just had to run out the clock. He chose to take the near maximum penalty just so he could plan for it instead of being surprised in a later year with a retirement. Ironically Suter has played to the same year of the end of his 13 year deal and Parise was only one year short. Criticism should be high no matter the buyout cap hits, but obviously we're too nice.