For iPod to mac transfer, I recommend Xilisoft iPod Rip for Mac



It enables you to Copy ipod to mac - backup iPod, copy music, video, movie, photo, podcast and TV program from iPod to Mac, iPod to iTunes and Mac to iPod.

* iPod to Mac, copy music, videos and photos from iPod to Mac
* Mac to iPod, transfer local files from Mac to iPod and iPhone
* iPod to iTunes, import iPod/iPhone audio and video files to iTunes
* iPhone manager, manage your iPhone as a portable disk



free Download

Tip: When this iPod Rip for Mac is started, it will modify the automatic synchronization of music/video to manual synchronization between iPod and iTunes.
So you don't have to worry any data loss. Proven easy and safe.

Hope this can help.