Holland is a great GM in my opinion. The Wings just had a bad run of luck of players not living up to their potential (and LTIR issues). You can tell he learned from those issues because he didn't hang on to Filppula or Hudler like he did with Helm and Tartar and he let let Pulkkinen and Sheahan go after 1 season of not being able to hit the net.
Its becoming evident in the Cap-Era that the only 2 ways to be anything close to a dynasty anymore are to either 1) lock up a generational talent or two long term and hope that you can randomly draft/sign enough serviceable 'depth' players that you can string together a cup run every couple years (Chicago, Pittsburgh, Capitals) or to sign a young core group of top six talent to long term middle of the road amounts and hope that they continue to develop and give you a window opportunity for a couple years (St. Louis, Los Angeles, Nashville). Obviously one of these approaches works better than the others, but nobody knew that back in 2005. The players Kenny bet on 8 years ago did not pan out, but I think all of his recent moves shows he's learned from that process and has changed tactics.