I've used this iPod/iPhone to mac tranfer program. It works just great. http://www.gutensoft.com/Utilities/4Media-iPod-to-Mac-Transfer.html
How to transfer all music, photos, videos, podcast, and TV shows on your iPod back to Mac completely and safely, and add them to your local iTunes library, step-by-step: http://www.gutensoft.com/Guide/How-to-transfer-music-videos-photos-on-your-iPod-iPhone-to-Mac.htm
Nice video guide, thank you. This iPod to mac transfer program works perfectly fine, too http://www.gutensoft.com/Utilities/4Media-iPod-to-Mac-Transfer.html My friend recommended it to me when my mac crashed. It can help easily transfer all music, photos, videos, podcast, and TV shows on your iPod back to Mac completely and safely, and add them to your local iTunes library. Also, you can use it to transfer files from iPod to iTunes or from Mac to iPod in a direct way. The great thing is that it won't cause any deletion of any files while transferring. Best luck!
Movavi VideoSuite gives you SIX amazing tools for video convert,capturing, editing and processing in a single package. It lets you: * Capture video from your digital and web cameras ; * Convert video to run on any mobile device ; * Split and merge video files ; * Add filters and special effects; * Rip, backup and copy DVDs; * Burn data, audio, and video CDs and DVDs ; * Create classy video postcards . http://www.gutensoft.com/Multimedia/Movavi-VideoSuite.htm
iPod 2 iPod will automatically display all files on both iPods, compare songs against two at once, remove hundreds of duplicates within one iPod in seconds, sort by Artist, Genre, Album, or even grouping of similar songs. All you need to do is simply to drag and drop what you want between iPods.Slick. Free download it at http://www.gutensoft.com/Utilities/iPod-2-iPod.htm to try.
How To Copy Music From iPod To Computer