The easiest way to get a random set of stuff onto the iPod is to make a smart playlist and ask it to pick random songs up to the size limit and then only add that list. Haven't worked out how to make it re-pick the list though, so it may be that I have to make it every time. Or simply not bother.
I just got an iPod mini for my son. I am infuriated at how iTunes takes mp3 without id3 tagging, and flattens the nested dir structure into an amorphous list of tracks. If you don't know genre/artist/composer info in the .mp3, the iPod seems to make the worst choice of outcome: preserving the dirnames would have preserved the difference between beethoven/fifth/track1.mp3 and little_richard/best_of/track1.mp3.<br /> <br /> Otherwise, a mighty fine beast.