not having an ipod i am just going by what the player i have does.
and you need to sync your songs with it. go in the the sync properties options and set the auto sync options to make one playlist, then send that playlist to the portable all the time.
you just edit that one list or you add sub lists under it so each time you sync that one list all the songs on it and the sub lists. and the songs on them will be sync'ed to the portable.
if the songs in the list are already there it wont add them again.
it just adjusts to what the playlist for it says, if you move it to a new list it will fix that also on the portable.
this never adds and albums and album playlists to my portable,
try it with yours and see if that will fix your headache.

not having an ipod i am just going by what the player i have does.
and you need to sync your songs with it. go in the the sync properties options and set the auto sync options to make one playlist, then send that playlist to the portable all the time.
you just edit that one list or you add sub lists under it so each time you sync that one list all the songs on it and the sub lists. and the songs on them will be sync'ed to the portable.
if the songs in the list are already there it wont add them again.
it just adjusts to what the playlist for it says, if you move it to a new list it will fix that also on the portable.
this never adds and albums and album playlists to my portable,
try it with yours and see if that will fix your headache.
8)