Update/backup iPod via iTunes on virtual Windows XP?
Is this possible? Legal? If so, what are the drawbacks and tricks


As of OS X Lion 10.7, the EULA permits you to use the OS in two virtual machines, on Apple hardware:


  (iii) to install, use and run up to two (2) additional copies or instances of the Apple Software within 
  virtual operating system environments on each Mac Computer you own or control that is already 
  running the Apple Software.


This was first allowed with OS X Server 10.5, and both VMWare Fusion and Parallels Desktop allow you to easily setup an OS X guest machine, as does VirtualBox

An OS X guest on non-Apple hardware is possible with some fiddling, but is in violation of the software's EULA (i.e doing so is of questionable legality..)



iTunes, running in a VM, will be able to see the iPod/iPhone/iPad. As long as the USB can be connected to the VM. So this depends on which setup you are using. The above should explain the legalities of the OS X and VMs.

You can install Linux on Apple hardware, then run a VM of OS X (10.7 and above) on the machine to be able to use iTunes to keep the library in sync and updated, etc., and it won't cause you any issues.