Playlists that also remove tracks from the iPod?

[Kosh]

I listen to a lot of audiobooks (used to listen to the CD, but now I've ripped 'em and listen to 'em from the iPod) in my car.

I have set up a playlist for the book I'm currently listening to, and have it set so that if a track's playcount is 1 or higher the track is removed from the playlist. this makes it handy to keep track of where I stopped, because I'll listen to music through the course of the day at work, and then listen to the book again on the way home.

However, I'd like to have the files removed from the iPod and simply left in the library on my computer, when I sync up the iPod at night.

Is this possible?

 

[dcmacnut]

Add an extra field to your playlist, such as "genre is audiobook" or something. that way only your audiobooks are put in that list. You can uncheck the track, and then enable "sync only checked songs" in your iPod preferences. All unchecked tracks will stay in iTunes, but will be removed from the iPod. I do that for my audiobooks and podcasts.

To uncheck several tracks, ctrl-click (or command-click) on one and it will uncheck or check the entire playlist.