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Assuming a sleep state: I would setup a service on the server.
Create service element that checks for external content and delivers processed files to an "outbox"
Create second service element that allows for a "connect back" from the kindle and delivers waiting files in outbox.
Create simple script attached to "wake up " event on kindle to attempt polling the NAS service.
You have the devices, know the final processes you wish to be undertaken, and all the event structures are already in place. Solution is half-way there. Little bit of coding and you are golden.
I would do that.
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