It seems weird that the robot is supposedly running autonomous, but that shouldn't even affect anything, because this robot has no autonomous mode. It is using the command based system, so it should keep running the teleop drive command even while autonomous is running because that is the default command for the drive subsystem.
Here is the code for the robot, but I don't think it is the cause of the problem:
https://github.com/RobotsByTheC/DemoRobot2015
I still have a hunch that the problem is related to the DS freezing. It definitely was not frozen because the laptop CPU was maxed out, so it seems like there is some bug causing it. It probably doesn't cause any anomalies in the logs because only the UI is freezing, but this might be affecting something. I'll try to reproduce this problem later this week, but it might be difficult because there is much less interference at the school.
Another weird thing I noticed in the logs is that the DS seems to be constantly reenumerating the joysticks and printing out the list. This happens even when the connection is working well, but it doesn't happen when using the 2015 protocol (with a roboRIO).