Proxmark3 kit would be nice ~ $500 when its all said and done, if you buy it outright and not build.
Rubber Duckies ~ $37 each, I would get 3-4
Pwn Pad ~ $150 for nexus 7, software free - I know several of us have some already, but might be nice to have a couple owned by the assessment and around in case we all get kicked off the team one day, or die in a fiery crash trying to decide where to eat in Ephraim.
I can think of various other little hardware trinkets I want to experiment with, and I'm sure others have ideas as well, so I would make sure you allocate a few hundred bucks for things like that.
Other than that I think shrinking the strike package is the priority. I kind of like that we crack passwords with low power. It makes the point about how weak those passwords are, even more poignant. That said, I want more of them!