Free agency has been a completely different game since the cap as well, the contracts are longer so there's less options during the off season, and more competition for players. We don't have young superstars to lure in free agents, there's lots of other exciting teams to choose from.
I don't know that I can say with certainty that Holland is the best GM, but I think he's done very well considering the circumstances.
Some of those "circumstances" were his fault. Keeping Cleary, Sammy and Bertuzzi around for too long. Trading a first rounder for Quincey. Spending too many trade deadlines on the phone ordering pizza instead of doing his job.
His defenders make it sound like he's a victim of bad luck or something. He's made his own troubles the last few years. Yeah, there were some bad breaks in there but he's not absolved of guilt.