The LW playlist in iTunes is purely a reference to the files in LW's Dwnld folder. You'll need to import the songs to iTunes in order to get them to your iPod. One way is to just drag & drop the files onto the iTunes application. iTunes will then import them to its own library. You can go to LW's library, select Saved Files, then select a file to the right of it, then press the Browse button. This will open the LW Dwnld folder up for you. Then just Drag & drop onto the iT app. I can tell you're using WIndows b/c Mac OSX users don't have this issue. iTunes will automatically import the songs directly from LW's dwndls folder in osx.