Oh,baby,
To save all your troubles ,I'd like to share you the powerful tool called 4Videosoft iPod to Mac Transfer .


4Videosoft iPod to Mac Transfer characterizes the main feature to transfer iPod files to Mac. More specially, this iPod to Mac Transfer software gives you access to transfer iPod movies, music, picture to Mac directly for the better storage, lest the iPod damage, or something else.

* Transfer videos, music, picture from iPod to Mac
* iPod to iTunes
* Support multiple iPods

Many iPod users have asked this.
It won't be a problem if you use AVCWare Mac iPod to iPod/Computer/iTunes Transfer.
It automatically transfers your iPod and iPhone music, video, playlist, photos to Mac and iTunes. Backup all your music and video in a couple of clicks. Really makes music and videos sharing pretty simple and enjoyable. Wish this can help and good luck.

I think its step by step guide is most helpful.
http://iphone-to-computer.net/transfer-songs-videos-photos-playlists-from-ipod-to-mac.html

It is easy to use and you can try it now.
http://www.google.com/search?hl=en&newwindow=1&q=site%3Aiphone-to-computer.net++avcware+ipod+transfer&btnG=Search&aq=f&oq=&aqi=