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If I have a home server, could I connect via VPN from any other computer and sync my device in iTunes (on the server)?

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Are you trying to imitate the sync over WiFi or sync over USB? – Doug Harris Dec 20 '11 at 14:06
Either one would work. – Jesse Dec 20 '11 at 14:58
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No, you'd also need some way of forwarding your USB port from your local computer to the remote computer1.

There are a few commercial applications2 that does USB over the net but a quick glance seems to indicate that they let you access USB devices on the remote computer locally and not the other way around.

1 When you say VPN I assume you also use some kind of remote desktop software.
2 http://www.usb-over-network.com/usb-for-remote-desktop.html , http://www.incentivespro.com/usb-redirector-rdp.html

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