And if all that comes together, we'd still have to synchronize over the phone.
The current solution is much simpler: I gave her a large enough SSD card to store months worth of pictures and fly over here every once in a while to visit and copy over everything to her PC etc.
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It gets shared with your other devices (iPad, iPhoto etc.) It's still not ideal, but getting stuff from the device to her computer has always been the biggest issue. After that, I take over with remote login.
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Except that, AFAIK, it doesn't share yet to Facebook etc. It shares between your own personal devices instead. That said, the turd case is something I hope they will solve eventually.
For one: you have to do it for all pictures individually (at least how you described it.)
For two: you need to remember to do it.
Don't underestimate the barrier of one additional click/action. Amazon with one-click (and Apple with iTunes) learned that very early on.
Initially I hoped to have fixed the photo upload problem by installing an EyeFi. It's wonderful when it works, but you need to keep the camera powered on the study desk next to the computer on to make it do its magic. One hurdle too much.