I think you can have a try with the professional tool called 4Videosoft iPod
4Videosoft iPod Manager is compatible with all iPod/iPhone devices, iPhone OS 3.0/3.1, iPod Firmware 3.0/3.1. Associated with friendly interface, it is really easy to use this iPod Manager. Only in a few clicks, you can complete the iPod management. Moreover, all functions for iPod are same with iPhone.
* Convert DVD/video to iPod
* Backup iPod files to PC
* Import computer file or folder to iPod
* Applicable to iPhone as well