So the one thing keeping me using Windows on my laptop when I'm off in the wonderous world of California was having to use iTunes to keep the music on my iPod fresh. But now, no longer, as I have been able to successfully sync my iPod with iTunes running under VirtualBox!
It turns out that it was actually working fine all along, but due to a bug in VirtualBox the VM would grind to nearly a halt, so it would look like it was frozen up. Running VirtualBox on my much faster desktop system resulted in perfect execution.
I guess I'll just have to upgrade my lappy to a shiny new Lenovo X200.