You are only giving me one log file and not the whole set of 6 log files - so period of time covered is shorter
The 13th january log whilst does not go back to time of launch and so cannot see the network interface detection, shows working uPnP automatic mapping to public port 23885 and the connectivity test was successful
Jan 13, 2019 20:49:33.590 [5440] DEBUG - HTTP requesting PUT https://plex.tv/api/servers/fe85bbf44688d7690cfe8680942873adbf2621e8/connectivity?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx&asyncIdentifier=6f347a12-aecf-4120-987f-d6a4e36d355b
Jan 13, 2019 20:49:33.805 [5440] DEBUG - HTTP 200 response from PUT https://plex.tv/api/servers/fe85bbf44688d7690cfe8680942873adbf2621e8/connectivity?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx&asyncIdentifier=6f347a12-aecf-4120-987f-d6a4e36d355b
Jan 13, 2019 20:49:34.032 [5736] DEBUG - Request: [34.245.172.51:38852 (WAN)] GET /identity (14 live) TLS Signed-in Token (Pjbracer1)
Jan 13, 2019 20:49:34.036 [1276] DEBUG - Completed: [34.245.172.51:38852] 200 GET /identity (14 live) TLS 3ms 386 bytes (pipelined: 1)
Jan 13, 2019 20:49:34.123 [1740] DEBUG - EventSource: Got event [data] '<Message address="82.19.xxx.xx4" port="23885" asyncIdentifier="6f347a12-aecf-4120-987f-d6a4e36d355b" connectivity="1" command="notifyConnectivity"/>'
Jan 13, 2019 20:49:34.123 [1740] DEBUG - PubSub: Got notified of reachability: 1 for 82.19.xxx.xx4:23885
On the 9th there was a different wan ip address and different wan port used
Whilst the log shows successful uPnP mapping, attempt to connect to your server through that wan ip and wan port failed. In this log we have the network detection and it shows Ethernet 2 not used because of no gateway and instead virtual switch used on 192.168.1.225 vEthernet (Broadcom BCM5716C NetXtreme II GigE (NDIS VBD Client) #35 - Virtual Switch
Plex Media Server ignore all network adapters with names starting with v because they tend to be not actual adapters to use
Try renaming it - may be that was what you did for the 13th Jan