Instead of just having the program files on USB memory stick could you have a had a custom bootable linux environment instead - then getting the environment set up would just be a case of plugging in to a PC and booting up. Sometimes getting to the point where you start programming can be hard.
I'd say it's one of the biggest barriers to entry out there. Getting a dev environment set up for anything other than hacking a Wordpress template is non-trivial for most.
I use the stuff at PortableApps.com quite often with consulting clients who need Firefox/Audacity/Gimp in a hurry. Could there be a portable Ruby/Python/Django dev setup that could get a novice going quickly without having to install a bunch of files?
I work on Debian Live, a framework for building customised live systems (we also make "official" live images as a special case). Something like this is easy to make and maintain using it.
Just a thought.