I have been trying to update the music on my 3rdGen iPod, copying from my iTunes library. I have given up on using the "sync" options because of unpredictable behavior (for example, after taking hours to sync my entire library, I then wanted to add an album, so I selected "sync selected ..." and it erased EVERYTHING except the new album).
So I've decided I need to use manual mode ("manually manage music and videos"). But even with that, I'm experiencing behavior that doesn't seem "manual". To wit, after selecting most of my songs and adding them to the iPod, it correctly copied them over, but did not have room for them all. Fair enough. So I wanted to delete some songs from the iPod (drag them to Trash) and manually add back some of the ones that couldn't be added in the big "add" procedure. Deleting worked fine, but then iTunes automatically started adding the songs that it didn't have room for initially. Of course there's not room for them all, so I'd like to select which ones to add. But iTunes knows better. Is there a way to circumvent this ?