When writing the media database to my iPod, gtkpod 2.1.3 usually crashes. This happens on various iPod types, including xA477 (2GB 2nd gen nano) and xC297 (160GB classic). I'm running Xubuntu 13.04 (Raring). Details are attached to the launchpad bug report:
https://bugs.launchpad.net/ubuntu/+source/gtkpod/+bug/1245234
Have you tried 2.1.4, in case its an issue already fixed?
I tried 2.1.4, but I can't tell if the code that crashes is ever reached because dropping files and saving changes both fail for other reasons in that version.
Last edit: Forest 2014-01-29