So far I have found 5 playlists on my iTunes library that won't sync to my iPod. I have no issue with my previous iPod or my iPhone with those playlists but only with my late 2009 issue iPod classic (160GB).
I have this problem, too. Many of my Smart Playlists on iTunes 9 do not appear in the Devices/iPod/Music tab Playlists: list. Thus, they cannot be symced to the iPod (Classic 80). All of the non-Smart Playlists appear.
Anybody have any thoughts?
I'm thinking of reformatting and reloading the iPod.