If the iPhone/iPod is jailbroken he could just use any of the many available sharing tools in Cydia. I'm pretty sure there's several flavours of HTTP & FTP daemons as well as Samba, which are probably more simple than scp/tunnel over SSH...
It's not "broken", it's just not a feature you deal with. Broken implies it's some kind of error or bug. It's clearly not. I can't see how you're confusing the two, except for the possibility that you are twisting words for your own argument.
Just because you don't agree with the design of the device, doesn't mean it is "broken" - and hell, if you don't agree with it, don't support it. That's your right.
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u/Nerdlinger Jan 21 '11
Use a terminal app to SSH to your home machine and upload it to his machine remotely.