Currently, I have a top level playlist called "All" with several child playlists under it. How can I setup the "All" playlist so that it randomly plays one track from a child playlist and and then another random track from any other child playlist? Right now, it randomly picks a child playlist and plays every track in that playlist before moving onto the next one.

I remember being able to do this with 1.03??

You can turn on Shuffle from the front panel instead of trying to tag each of your playlists as "always randomize"...