Petry/Holl he could've done without, but outside of that I think he's been fine.
Free agents for a rebuilding team are always tough, you need vets, but you're never fully sure what you're getting after they get their deals. And then you typically have to pay premium on top of that. Compher & Copp could've turned out better, but they were playing well on their previous teams.
Someone said Holland left the Red Wings in shambles, and I completely agree. As a GM, you can't start with a much worse situation than Yzerman did. Whoever took over pretty much had to wait out a couple years and watch the team lose. After that they haven't been horrible.
A bubble team is on par with expectations where they should be at this point IMHO. There's more playoff-capable teams in the League than ever before in my opinion, it's hard to make it, and it's especially hard to break out of the bubble. You need big time difference makers and those don't grow on trees. Patrick Kane was worth a shot.
I'd give him a chance to try to get them over the hump and see some of those prospects get in the action. Whoever gets hired as the next coach will be a big deal as well. If he fails with these things then it's time to move on.