Hey Code Monkey!
I'm plugging along on my Classic 160 with a whole slew of nested live updating playlists resulting in a countdown playlist of 170 or so songs. I have been curious what your take on the ICloud storage is and what you think it points to for the future for users who live and die by these smart playlists and the metadata that drives them. Its not clear that Icloud has any smart playlist considerations.
My dream Ipod I think would allow me to customize the display so I can have an additional screen of metadata available on the ipod such as last played and playcount. I really worry about the eventual neeed to replace my 160 when the time comes. It's really a perfect device for me now and I love the rating display on the now playing screen. It saves me clicking into a track to check rating each time a new song comes up.
I really hope that Apple does not forget about smart playlists users going forward.