If you know java, I would suggest go straight to that. Don't even install the Labview DVD, its not necessary. Instead download and install the "FRC 2014 Update suite".
https://decibel.ni.com/content/docs/DOC-34731. This is required no matter what language you use and includes the imaging tool and drivers station program. At the minimum the driver's station needs to be installed on the 2GoPc. I agree that its good to put your development environment on another computer, maybe one with a little more horsepower. As you discovered, to install programs on the classmate, you have to put them on a USB stick.
As for java, Here's the link for getting started with java:
http://wpilib.screenstepslive.com/s/3120/m/7885
The tutorial there will get you a driving robot.