I'd put him out of everybody's misery.
Friend gave me their old iPod Shuffle, which was nice. Loaded iTunes*, and the damn thing would NOT show any music loaded. Uninstalled, reinstalled, restored, etc. iTunes showed the player connected, all's well, but would NOT put music on it.
Dug around a bit, and found that apparently there's some bug in the versions later than 7 that will not work with the Shuffle. Very effing nice of Apple, isn't it? And from what I can tell, the damned problem has been around a while, Apple just hasn't bothered to fix it.
Yeah, whacking Jobs would make Bill Gates happy; I don't care.
*iEverything my ass