Alright, so I'm still using a 20GB Xbox 360 (maybe a year and a half old, Microsoft gave me a new one after mine redringed). I have one messed up wired controller (RT only somewhat fully reacts while pressed, sucks for racing and FPS) and two wireless controllers that are both kinda messed up. The black wireless is essentially fine, but the RB is consistenly getting worse and worse and I imagine it will stop working at the some point. The white wireless has fully functional buttons, but it only turns on 1-in-5 times So a fresh controller and a bigger hard drive are both a big plus for me and then all the other cosmetic stuff are cool too. 
 
Here's what I think we're looking at for the GameStop trade in:
 
Xbox 360 with wired- 100 
Two wireless controllers- 50 
One wireless adapter- 40 
20 GB HDD- 30 
Headset- ??? 
Mario Party DS, NHL 08, NHL 09, Yu-Gi-Oh! 2008, Guitar Hero II with controller- ??? 
 
So in total I have $220+ whatever the headset and 5 games with the guitar are worth. So that's basically $60-80 for a fresh controller and a 230 GB upgrade, which I both desperately need. My only worry is that they'll test the white controller and it won't turn on, but given my experience with GameStop (which was maybe 3-5 years ago), they couldn't give a shit about the quality of the stuff you're giving them. 
 
Thoughts?