Yeah, I think newer iPods and iPhones don't work with Linux. They appear as a mass storage device, but they have a proprietary index file, and refuse to play music that's not in the index. And iTunes' compatibility with Wine is a bit hit-and-miss.
You can download an evaluation version of Windows 7, http://technet.microsoft.com/en-us/e...442495?lc=1033
. In order to use your iPod with VirtualBox you will have to use the PUEL version of Virtualbox, downloaded from their website; the Open Source Edition (included in Linux distributions) doesn't have USB support. (Of course, you probably don't want to have to pay $$$s for Windows to use your iPod, and you're not supposed to keep running the evaluation version.)
For those running Linux, generally it's a good idea not to buy devices whose manufacturers go out of their way to tie them to their own software, and then don't release said software for Linux.