I've just got the 310, but iPod tracks are an arcane mystery to me.
It seems hell-bent on organising every track in alphabetical order no matter which CD or playlist it come from. With the music I've got, that means random tracks from Wagner's Ring mixed in with random tracks from Handel's Messiah and random tracks from The Magic Flute, and indeed random tracks from every opera, oratorio, symphony, cantata and whatever, that I own.
This seems to be its default setting, and it starts to play without waiting to be told, so if I'm starting from scratch, I'm forced to listen to a particular track from Parsifal that just happens to start with the word "Aber", every single time. Getting out of that and into the playlists menu isn't easy, and then, once a playlist is finished, it's all to do again to find another playlist. (Unless you want to listen to the same playlist on a repeating loop, which it will do if you don't stop it.)
It's probably the way the iPod is designed in the first place, but you'd think the designers would realise that most people want to listen to an album or a playlist, not to have random traks handed to them in arbtrary alphabetical order.
Rolfe.