This isn't a defense of Holland, but rather an observation. I do think that it is much easier to trade a player if you just walked in to become GM, opposed to trading a player that you personally signed, and quite possibly said things like "we want you to finish your career as a Wing" to. Not that Holland said that, but I have to think that things like that have to factor in on your decision making. Also, in Edmonton they are in win-now mode with McDavid, here we were re-building where I'm sure the urgency to move a contract like that was significantly less.
With that said, I agree with your point. Yzerman coming in means he has no emotional ties to any player, and that's probably a good thing.