FWIW. I finally got round to buying an MP3 player (not an Ipod). It has 1GB memory and I thought it would be an idea if I could create a randomised list of tracks from the CD's in my collection. (I am well aware that many of the larger players have so much memory it can be almost difficult to fill them completely with your own collection). Anyway ...
I wrote a simple GUI program that will allow you to specify a start directory, the filetypes(s) you want to download and (possibly) how many bytes you want to download. It then builds up a list of all the files in memory and then selects and copies them randomly to the MP3 player.
What's interesting in a way is the fantastic speed with which it builds up the list of available files in memory (using a variation of Jeff's LISTALLFILES).
Anway, anyone interested in getting a copy, send me a note.