Something out of the recent bunch of upgrades to Ubuntu, VirtualBox, iTunes, and the software running on my iPod Touch is a bad thing. A very bad thing.
Ten to fifteen minutes to sync, and then after a few minutes, and anywhere between twenty and four hundred songs later, it hangs, and hangs, and then finally iTunes gives me a "this device cannot be synced. Timed out".
I'd like to bitch at Apple, and have a go at that old "it just works" thing, but unfortunately Apple only account for fifty percent of the recent changes which may or may not have buggered it all up for me.
Ah well, back to troubleshooting, and trying different versions of all of hte above, plus different USB cables/ports/powered hubs.