copy the songs to your hard drive; import them into your itunes library; make sure there is a check mark next to the ones you want to put on the ipod; then sync the ipod.
copy the songs to your hard drive; import them into your itunes library; make sure there is a check mark next to the ones you want to put on the ipod; then sync the ipod.
I think you can highlight everything on the remove, rightclick and remove/delete. Do not remove from Itunes library, although even that shouldn't remove it from the hard drive.