I used Amarok with my iPod Shuffle, worked great. I've written some instructions on how it can be made work, if you take some time to search among the threads. Rhytmbox or GTKpod or the other apps seem to work not-so-well compared to Amarok, so if you have a chance, at the time it may be easier for you to use Amarok. With Ubuntu's version of it it's pretty easy to auto-detect your iPod, save the settings of pre-connect and post-disconnect (to mount the device when Amarok connects to it, and umount the device when Amarok disconnects it - automatically) and just use the deviec(s). And as far as I've tried, Amarok tends to work more reliably than the other front-ends; though I'm pretty sure most of them use the same libraries (libgtkpod).
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