Generally I like what I perceive to be "thoughtful picks" and dislike picks that seemingly just fell into our lap. I think Holland was doing a lot of the later towards the end of his career...
Examples of a thoughtful pick: Seider or Bertuzzi. Both taken higher than expected, both show Holland's/Yzerman's willingness to buck popular perception and go with the player they like.
Picks I didn't like:
1. Zadina: Sure seemed like he just fell into Holland's lap and he couldn't resist.
2. Veleno: Same as Zadina.
3. Jurco: Similar to Zadina and Veleno, felt like Holland just opted to take the kid with the cool youtube dangle vidoes becuase he had no one better in mind. Consider that we had 3 second round picks that year. We came out of that second round with Jurco, XO, and Sproul... We passed on Boone Jenner, Victor Rask, Brandon Saad, Markus Granlund, Joel Edmundson, Matt Nieto, William Karlsson, and Nikita Kucherov in that round for those three. Holy lerd how were we not able to identify one decent player with any one of those 3 picks? There were plenty there. These are the kind of things that set your franchise way back. Whiffing on three swings in the second round. Imagine if Karlsson, Saad, and Edmundson were on our roster right now.... let alone Kucherov...
Player development just isn't that easy to project. Ok Kucherov and Karlsson immediately showed great promise after they were picked, as did Saad and Granlund after 2 years. But Jurco, XO and Sproul had better junior careers than the others. When they were tearing up juniors winning all kind of awards, it would have been hard to project Jurco, XO and Sproul all amounting to so little. At 19 & 20 they were better than most of their peers. Sadly Jurco had his head broken by Babs & Blash and has never found confidence since, XO just never got any better at skating, and Sproul seemed incapable of developing any defensive awareness, which really should have been coachable. That said, I think all were also caught up in some awful asset management by the wings. All 3 would get much longer looks and better chances of development on this team now.