iPod pros - any way to easily fill a small iPod with random selections from iTunes library?

[RAMd®d]

I use the Smart Playlist gambit.

For just the reason you mentioned-- using multiple Genre rules, I can taylor the semi-random filling of my 'Phone.

I have some permanent playlists and Smart Playlists for Random fill and specific "Must Have" categories (not genres). The latter I can update live by assigning stars to the music. Selecting one or more stars will put a song on one of five Smart Playlists.