When i drag an drop songs from my itunes library 'i select all' and drag the whole lot over to the ipod icon... however i find that sometimes the songs are just adding and not overwrighting as i would wish....
right click on the ipod icon
then in the settings there is a thing for it to automatically sinc and duplicate the library. that should delete all songs not in your library.
If not, it is a setting somewhere in the ipod options.
