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I just had this issue- I bought a movie off iTunes, and could view it on the computer, but it wouldn't go on to my iPod. I looked around and found instructions to open iTunes and on the home page of your iTunes where it shows you how much space you have, you can restore original settings, etc., if you click on "manage iTunes manually" or "manage music and videos manually" and then click apply you will be able to move your movie on to your iPod. In your iTunes library you just have to drag and drop the movie onto the iPod icon that appears in the left menu when your iPod connects to iTunes. It took about 10 minutes for mine to fully upload onto my iPod- so make sure you wait to disconnect until it tells you to. I hope this helps! What I read is that when managing the music and videos manually instead of it doing it automatically, you can move the videos and music as you'd like.
Not sure if you have 1st or 2nd gen
These manuals suggest that when you connect to itunes, it automatically deletes all songs not in your library. Otherwise i don't see a format option unless the drive shows up in my computer and you can format it there (right click).
It basically suggests that you have to use one of the manual methods on the pod or computer to delete songs.