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Do you have remote access to his computer? Could you set that up? That's what I did for my parents before we moved close enough to drive between our homes. The parents job is to plug the USB cord from the computer to their device (Kobo or whatever), the childrens job is to remotely access the parents computer over the internet, do all the transferring and whatnot, then tell the parents to unplug their device and enjoy!
We all run Linux in our family, so remote access was trivially easy. If you're running Windows instead, remote access is still doable, but will not be as straightforward. You'll probably have to buy and install some proprietary remote access app, unless you're running the expensive "Pro" version of Windows, which comes with "Remote Desktop" I believe.
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