It is very hard to know what is happening here.
First thing: the computer running calibre seems to have 2 IP addresses on the same subnet. That isn't a good thing. According to the debug log, CC sees:
Code:
WDConnection: Broadcasting ...
2016-12-21 11:50:28.941: WDConnection: MDNS ServiceAdded. name=Books in calibre (on ***** port 8080), address=192.168.0.100, port=8080
2016-12-21 11:50:30.991: WDConnection: received broadcast response calibre wireless device client (on *****);8080,9090, address 192.168.0.101
CC then attempts to connect to the .100 address, which doesn't work.
Later we see CC attempting to connect to the .101 address and succeeding
Code:
2016-12-21 11:51:11.551: ContentServer: creating connection to http://192.168.0.101:8080/
2016-12-21 11:51:11.705: ContentServer: checking authentication
2016-12-21 11:51:11.895: ContentServer: creating connection to http://192.168.0.101:8080/
2016-12-21 11:51:12.073: Feedparser got category string urn:calibre:main
2016-12-21 11:51:12.101: Opds DataManager addData: start=0, finish=8, url=opds
As for the wireless device, something similar is happening. CC sees:
Code:
2016-12-21 11:58:30.315: WDConnection: MDNS ServiceAdded. name=calibre smart device client (on ***** port 8090), address=192.168.0.100, port=8090
2016-12-21 11:58:32.459: WDConnection: my ip address is: 192.168.0.102
2016-12-21 11:58:32.464: WDConnection: trying server address 192.168.0.100 port 8090
2016-12-21 11:58:35.472: Attempt to connect resulted in exception
java.net.SocketException: failed to connect to /192.168.0.100 (port 8090) after 5000ms: isConnected failed: EHOSTUNREACH (No route to host)
The error EHOSTUNREACH says that no computer with the IP address reported by calibre (.100) is visible on the network. This is (again) probably caused by the calibre machine having two IP addresses. Many routers cannot support two IP addresses pointing at the same MAC (device hardware) address.
In another instance, CC seems to be on the right network but calibre doesn't answer the connection request.
Code:
2016-12-21 12:00:42.929: WDConnection: MDNS ServiceAdded. name=calibre smart device client (on ***** port 8090), address=192.168.0.100, port=8090
2016-12-21 12:00:44.984: WDConnection: received broadcast response calibre wireless device client (on *****);8080,8090, address 192.168.0.101
2016-12-21 12:00:45.006: WDConnection: using broadcast server address 192.168.0.101 port 8090
2016-12-21 12:00:49.984: WDConnection: my ip address is: 192.168.0.102
2016-12-21 12:00:49.986: WDConnection: trying server address 192.168.0.101 port 8090
2016-12-21 12:00:54.990: Attempt to connect resulted in exception
java.net.SocketTimeoutException: failed to connect to /192.168.0.101 (port 8090) after 5000ms
This could be caused by calibre listening on only one of the IP addresses, by a firewall problem (yes, I saw you said you disabled the firewall), or by a router problem dealing with one computer on the subnet with two IP addresses.
In terms of solving this, the first thing to do is to ensure that the calibre computer has one IP address on the local subnet. Once that is true then the problems might go away. If they do not then more work is needed.