I have been using a program called RestoreCD in conjunction with Pstart to autoplay my 80GB USB drive.
This program detects the version of windows you are currently on and then displays user defined categories and programs that you can install. This is great to display Windows version specific programs for user install (eg Acrobat 6 for Win 98, Acrobat 7+ for Win 2000+ etc).
You can customise tabs to keep categories seperate (eg Applications, Drivers, Utilities etc).
http://www.geocities.com/koolasnz/restore/
Free for personal use.