For the last year or so, I’ve been trying out various different methods for working with my iPod nano without relying on iTunes. (iTunes is slow and bloated, at least running under Windows, doesn’t run on Linux, and relies on proprietary DRM so it makes it very difficult for me to move music files between my laptop at work and my desktop at home or play them on other devices).
I recently went back to a project called Rockbox, which I used to run on an Archos Jukebox.
But now Rockbox runs on many iPod models, including my Nano.
It’s well worth checking out if you have lots of mp3 files and you move between machines. It can be installed from a Windows, Mac OS, or Linux host computer, and it relies on just treating the ipod as a drive when connected to PCs – you can move files on and off, with no need to rebuild any iTunesDB on the device, or having iTunes obfuscate all the file names and bury them in random directories.