Are you talking about your iTunes Music Library or your LW Library window. You've probably deleted the songs that you downlded after adding them to iTunes library. You can only transfer songs to iPod from iTunes Music Lib. (unless you use a 3rd party utility.) Why not share your iTunes Music Library & then all your songs will show up in LW's Library window.

If you want to extract songs from your iPod then you'll need a special 3rd party utility to do that. You should be able to find something here to do that: http://forums.ipodlounge.com/showthr...&threadid=4719 such as PodUtil or PodWorks & others; http://www.pure-mac.com/mp3.html