Best strategy for using iTunes on VirtualBox

Question

The scenario

• I'm a Mac user
• A friend of mine bought an iPod
• She is an Ubuntu user and by no means she wants to go back to Windows
• She doesn't have the money for a Mac
• Frankly, there's no real open source alternative to iTunes ( Genius Mixes anyone ? )

The question

• What's the best strategy for using iTunes on virtualized Windows using VirtualBox
• Is there a way for the iTunes Library not to be stored inside the VB disc but in the Ubuntu disc ?
• VB installed from the repositories doesn't support USB. I've heard that you can download a version that does. Is that true ?
• If so, does VB USB support syncronization of an iPod ?

Edit:

Functionalities not present in Amarok et al that comprise the full iPod experience:

• Genius mixes ( cloud, AI, collaborative filtering and recomendation )
• iTunes store
• Genius lists
• iPod software update
• Syncronyzation of podcast position
• Syncronyzation of audiobooks position
• iTunes iCloud
• Library consolidation
• etc

Answer 1

If you have VirtualBox installed, you can install the extension pack (also on the main page), which has USB drivers. It's a separate package because the licensing is different, but for home use, you should be fine.

There should be a dialog that lets you auto-mount all USB devices that match Apple's PCI vendor ID, which would actually redirect the iPod's USB connection directly into the VM.

As for storing the iTunes library on the Ubuntu disk, you should look into VirtualBox's shared folder capabilities, as I believe those would be the easiest way to get access to the host system's folders from the guest. Mount that folder to a drive letter, and iTunes should be able to use it (point to it in iTunes' library settings dialog).