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Well, I am at a loss. The fact that it works sometimes implies that the basic networking setup is correct, that CC can "see" the calibre machine, and that the firewall & A/V on the calibre machine are not blocking traffic. It isn't a protocol issue because both the content server and the wireless device work.
I don't know what would cause the intermittent problems other than the ones I mentioned above. Clearly *something* is blocking network traffic, probably the connection sequence. That can happen if something is interfering with the WiFi signal, the laptop wanders off into some very busy state such as doing a network backup, or the Fire does something similar such as syncing with Amazon.
You mention that the laptop is connected by both cable and wifi. That will result in the laptop having 2 IP addresses. It is possible that the Fire is trying to use both of them, which will not work. Calibre will also try to use both, which can lead to confusion about which to use when talking to the fire. Try disconnecting one or the other.
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