if you uncheck the song in your itunes library and then update the ipod the song should remove itself from the ipod. the only drawback is that the song will no longer be included when you play from your library, but after updating the ipod you can check the song again and all is well. just remember to uncheck the song again next time you update. :\

This is my routine. I hope I can explain it well enough to be understood.

I create a main iPod playlist for ALL the songs I want on my iPod, and other iPod playlists, such as "newest music." Any time I add music to the iPod, the songs first go in the main iPod playlist, then for the additional playlists, I drag songs from the main iPod playlist. In iPod preferences, I choose "automatically update selected playlists only" and choose the various iPod playlists. Any time I want to remove songs from the iPod, I delete them from the main iPod playlist, which automatically deletes them from the other iPod playlists and the iPod itself when it's plugged in. I can easily look at my main iPod playlist to see if it's getting too big for the capacity of the iPod and remove or add songs or albums as needed.

Sounds complicated but it works great. Hope this makes sense. It takes some initial setup but since my iPod can't hold all of my music, it's much easier than "manually managing" all the time.

The uncheck method is probably the best method. I hadn't even thought of that.

All it does is tell the iPod which songs to synch. It doe snot delete them on the computer, just doesn't synch them to the iPod.

They also won't play in iTunes when you have it playing on random though. iTunes will skip unchecked songs.