Nothing's a bigger waste in today's NHL than the "rebuild." You can flop all you want and end up with immensely talented players and still fail to win a Cup. Moreover, you can end up like Buffalo, Ottawa, Detroit and Montreal and not even qualify for the playoffs season after season.
Given that winning is difficult and limited to one club per season, it's probably important to consider other successes. Making the playoffs when you have a huge amount of dead cap is actually one sign that the team was well put together.
I don't see the Wild ever winning a Cup in my lifetime but I'd rather have a GM who adds talent occasionally than a GM who sends more away than he acquires. I do think Guerin has done pretty well overall and this summer will be the big tests: getting Rossi on a reasonable deal, extending Kaprizov or getting a "Martin Necas" if he can't, and adding a piece or two that can make the team into a legit contender next season.