manually adding/removing songs from iPod using ITunes

Question

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 ?

Answer 1

Looking at the iPod (in the iTunes session), notice that the songs that could not be copied over in the initial big "add" are greyed out. This means that they are queued up for adding to the iPod; which is why iTunes automatically starts adding them to the iPod when space is freed up by deleting other songs. Evidently this cannot be prevented. But it IS possible to delete greyed-out songs from the iPod (the same as non-greyed out songs, by dragging to the trash or right-clicking and "delete"). By doing this, it is possible to insure that songs I didn't really want are not automatically added (back to the iPod in the freed up space). This is not really the behavior I would hope to see when using a "manual" mode, but apparently it's the best that can be done.