Tux,
If you pull from my git repository of RobotPy, when you do make_dist.bat there is an 'install.py' in each of the dist directories that will let you upload stuff to the robot automatically. Just enter in your team number and it'll FTP stuff to the robot.
Additionally, my repository is updated to WPILIB v2262, whereas Peter's repo is out of date by at least two WPILib updates.
https://github.com/virtuald/RobotPy