If like me you manually add to your iPod, then it can be a real pain when iTunes decides it doesn’t want to recognise your iPod anymore, or you decide to get a new one or just want to get a song off there!
I recently came across EphPod (Win/Linux)…. and since I also have a MacBook Pro found iLinkPod.
I am not going to describe how to use it as I did find a good tutorial here. If you insist … here is a very quick ‘How-To’ for EphPod: find the music you want using the search boxes at the top, or the grid at the bottom for individual songs, and then Right Click and select ‘Copy Songs to Directory’, or alternatively press Ctrl + Alt + C. Holding Ctrl while selecting will allow you to choose more than one song/album/whatever at once.