I think he's done well. The bottom line is the team inherited was not going anywhere for a long time thanks to all the NMC Wilson handed out like candy. That's something you're also not taking into consideration. These players all had basically final say on where they went. You combine that with their age and salary and you were never going to have more than two maybe three options per each. Meier was the only one that didn't but let's be honest, there was no team control given the 10 million QO. NJ certainly wanted nothing to do with that qualifying offer. Who was Jersey going to give up that was reasonable? Certainly not Mercer or Nemec or Hughes. The only name left was Holtz, and we saw how that turned out.
The arguments about "well, this is what he SHOULD have done" is so pointless because you have no idea what the options were. Teams weren't necessarily going to give up more for more retention. Teams may not be interested in a declining player with multiple years left and it certainly doesn't mean they were going to sacrifice more of their future just to save a couple bucks now.
So many people here abide by what the HF board consensus is regarding who's worth what and 95% of the time HF is wrong, yet that's not us random couch posters who are out of touch, it's the professionals who actually talk to one another. The fact is Grier took a graveyard that had no prospects and a lot of aging contracts and turned it completely around in 2 years. No matter how much you want to nitpick every aspect of every trade, there is absolutely no arguing the results so far.