Chosen Solution
I was tearing down my steam controller to use its trackpad because my trackpad on the vive’s controller doesn’t vibrate. When I was tearing it down I went to take out the screws on the side, not knowing the bit wasn’t long enough (t6). It got stuck and I couldn’t get it out I even drilled around it to see if I could get it loose, unfortunately, the bits stuck and I can’t get it out. My brother own’s the iFixit kit I used, so I didn’t buy it.
I had almost the exact same issue with my recent tear down, those are VERY recessed. I was able to pull mine out with my side cutters as the bit was just long enough to grip in my case.
Looks like you may need to Dremel beside the bit a little so you can get a grip on the bit with something like I did.
It is mostly hollow void behind the back of the controller and the chutes the screws go into aren’t touching anything until you reach their full depth.