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No. CC won't change to allow intermixing of transfers by cable and one of CC's connection types. The difficulty is the high complexity of correctly managing CC's metadata and format steering when books arrives in an uncontrolled fashion. I am not going to take on that problem.
As for why the Fire sometimes doesn't connect: I don't know. Because it is intermittent I suspect something related to wireless band steering (devices connecting on different WiFi bands). It also could be related to interference from nearby WiFi hubs that the phone can handle but the Fire cannot.
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