Ubuntu works well with my 5G ipod.
First off, I am running Ubuntu 6.10.
I use gtkpod for the managing audio files. It automatically detects my ipod and it allows me to add and remove files from the ipod.
I use ipodder to set up podcasts for download.
I use GPixPod for loading my photos.
Haven't gotten into ipod video yet so can't offer help on that end.
But these other applications work well for me. gtkpod, the main program, and ipodder work flawlessly for me. I have seen glitches in the operation of GPixPod but no crashes from it and it has always worked in the end.
Hope this helps.