That should be “glad there’s NO DRM…”, of course. Missed the edit window.
It’s a playlist whose content is automatically assembled based on a set of rules, such as “Sally’s playlist = notes contains Sally” or “Classical music playlist = genre is classical.” So you don’t have to worry about managing the content manually.
Never tried using more than one iTunes account on one computer. Can’t see why shouldn’t be able to do it, though.
To expand, you then set up your pod to sync nothing but this playlist (or playlists). What gets synced can still be accessed by way of artist, album etc. on the pod.
And your playlists can be as granular as you want. I don’t know what the maximum number of rules is for a smart playlist, because I haven’t run into the limit yet. So you could set up Sally’s Ipod to sync:
- Sally’s 1960s R&B Playlist
- Sally’s 1950s Crooners Playlist
- Sally’s Baroque Composers Playlist
- Sally’s O.S.U. Microbiology Class Voice Memos Playlist
- Sally’s 1950s-1960s Surf Rock and Good Time Music Playlist
- Sally’s Public Radio Podcasts Playlist
This sounds promising indeed. I will spend some time investigating today. I want to group songs by artist or by album, so I hope this doesn’t mean I have to notate every single track in some way.
Thanks! Will report back.
All the data fields are available for use in the rules, so you can use “artist is Katy Perry” or “album is Sandanista!”
If it were me, though, I would think twice before creating a whole set of playlists based just on artist and album, though, because those fields are already accessible separately on the Ipod.
If you’re using Windows, Foobar2000 is probably the most powerful. To get it to do what you want, you’ll have to spend quite a long time setting it up and downloading the addons you want, but on the other hand, you can get it exactly how you want.
ETA By you, of course I mean your friend 
And to expand further, this works for “dumb” (ordinary) playlists as well. The takeaway is that each person should select and maintain a playlist(s) for themselves, and sync those.
That stupid checkbox on each item is iTunes worst feature – it’s too prominent, and leads everybody into thinking it’s important. Folks think it’s selection (it isn’t – it’s "sticky’). What it really is is a way to globally turn items on and off (i.e. for all users, devices, streamers, etc.)–which isn’t really a common thing to do. And it isn’t even really good for that, since you can ignore it on a per-device basis.