It won't be a problem if you use a professional iPod to iPod/Computer/iTunes Transfer.
It automatically transfers your iPod/iPad and iPhone music, video, playlist, photos to computer or iTunes.
It can backup all your music and video in a couple of clicks. Really makes music and videos sharing pretty simple and enjoyable.
It can also transfer files from iPod to iPod, from local computer to your iPod.
Wish this can help and good luck.
It is easy to use and you can try it now.
http://www.ipod-transfer-soft.com
I think its step by step guide is most helpful.
http://www.ipod-transfer-soft.com/ipod-to-computer-transfer.html