Actually, the more I think about it, the more it seems that trying to get the GUI to work with a remote server as the backend is a little too ambitiuos. Might be better to just create a "device" that connects to a remote server. That way you can just connect to the server in the GUI and copy books back and forth from the remote server, as you would from a device.
Much easier to implement and while it does not address the use case of running the server and the GUI simultaneously on the same machine, it goes a long way towards addressing the question of how to manage a calibre library on a remote, headless server.
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