I was able to find a simple, free program that allows easy transfer of audio/video files between an iPod and a PC (for later transfer to an MP3 player or flash drive). It allowed individual file transfer as well as the ability to sync both devices. I can't remember the name, but I found it at cnet dot com.

The particular program I used could be installed on a memory stick - so you don't have to install it on the PC to up/download files. You should be able to find it (it's been about a year since I used it).