I recently picked up an iPod from the TE member's market (iPod Nano Black 4G
hyeah: ). As I only have linux at home, I started running into issues while attempting to sync it with any of the available AV applications. Tried Amarok, banshee, rhythmbox. While some of them do allow you to put songs on the iPod, none of them allowed me to automatically synchronize podcasts and stuff (banshee does allow this feature but owing to the migration from HAL to DeviceKit it is currently hosed/partially working in the latest release of Ubuntu).
So with much sadness I decided to use iTunes for managing the iPod as God and Steve Jobs intended. I had a WinXP license lying around so I created the leanest possible Windows XP installation on VirtualBox (with nLite and other tricks picked up from lifehacker).
The issue was that I didn't really need all of Windows, just iTunes which should work with my iPod. To accomplish this I set a device filter on virtualbox to "trap" my iPod in the virtual machine whenever it was plugged in. The link below provides instructions for an older release of Virtualbox, but is should work even now.
Using USB device filters with Sun xVM VirtualBox - SearchServerVirtualization Blog
Now the best part is that Virtualbox supports something called seamless virtualization. Typically this allows you to blend desktop elements from the virtualmachine with your host. It can also be used to display only a specific Window if required. Once you've booted your VirtualMachine, you can select the window that needs to appear on your host OS (in my case iTunes) and press the host key + L (the host key is usually the right control key, but it can change. The lower right corner of the VM should tell you what the host key is).
Now you have iTunes pretending to look like a native linux application. If your virtual windows xp machine is running and you plug in your iPod, it should now show up in Windows and you can use iTunes to sync your tunes, podcasts etc.
I suppose other TE members use iPods with Linux too, what is your solution to obtaining an iTunes like experience? (Automatic synchronization, last.fm integration, podcasts).

So with much sadness I decided to use iTunes for managing the iPod as God and Steve Jobs intended. I had a WinXP license lying around so I created the leanest possible Windows XP installation on VirtualBox (with nLite and other tricks picked up from lifehacker).
The issue was that I didn't really need all of Windows, just iTunes which should work with my iPod. To accomplish this I set a device filter on virtualbox to "trap" my iPod in the virtual machine whenever it was plugged in. The link below provides instructions for an older release of Virtualbox, but is should work even now.
Using USB device filters with Sun xVM VirtualBox - SearchServerVirtualization Blog
Now the best part is that Virtualbox supports something called seamless virtualization. Typically this allows you to blend desktop elements from the virtualmachine with your host. It can also be used to display only a specific Window if required. Once you've booted your VirtualMachine, you can select the window that needs to appear on your host OS (in my case iTunes) and press the host key + L (the host key is usually the right control key, but it can change. The lower right corner of the VM should tell you what the host key is).
Now you have iTunes pretending to look like a native linux application. If your virtual windows xp machine is running and you plug in your iPod, it should now show up in Windows and you can use iTunes to sync your tunes, podcasts etc.
I suppose other TE members use iPods with Linux too, what is your solution to obtaining an iTunes like experience? (Automatic synchronization, last.fm integration, podcasts).