Virtual Windows system + ITunes.
I installed virtualbox 4 and set up a Windows XP. To use the USB drivers I installed the Oracle Expansion Pack. The Licence changes from OSE (Open Source Edition) to PUEL (Personal Use and Evaluation License).
Plugin the Ipod to your Ubuntu System. Start the VM with Windows and Itunes. Under "Devices" in the Virtual Box select your ipod nano. Windows and Itunes will find it.
I also shared my music-library with a virtualbox shared folder and mountet it under windows.
This works for me but I am unhappy with the situation too.
http://askubuntu.com/questions/26353/how-can-i-sync-with-an-ipod-nano-6g
Spotify
http://www.engadget.com/2011/05/04/spotify-launches-download-service-with-ipod-sync-puts-itunes-on/
PlayOnLinux (Wine frontend) > Multimedia > Spotify
http://www.makeuseof.com/tag/spotifys-free-version-working-linux/
VirtualBox windows on Ubuntu
http://www.blog.arun-prabha.com/2007/05/07/installing-virtualbox-and-windows-using-virtualbox-in-ubuntu/
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