Looked at the logs and they do show problems - but at this point i cannot see any clues in the logs.
The logs show PMS does an hourly refresh of the uPnP automatic port mapping and every hour it is successfully re-instating the port mapping of public port 11394 to the local
It was being refreshed at 49 minutes past the hour every hour and we have that sequence from October 18 04:49am onwards
I can see at 13:25 on October 18th you disabled and re-enabled Remote Access. There was a refresh of the port mapping done without error at 12:49 (36 minutes earlier). I cannot see any issue in the log before you disabled remote access and re-enabled it. We may need some Plex client apps logs as well in such cases eg cellular connection on iPhone or Android and getting the logs for that and the server before you disable and re-enable remote access. Also might help, is viewing the router uPnP port forward table to see if the port entry (in this case it was 11394 public to 32400 private exists in the router)
The reason i suggest looking at the router is because of this error when we went through disabling remote access
Oct 18, 2018 13:25:33.465 [11572] DEBUG - PublicAddressManager: Stopping.
Oct 18, 2018 13:25:36.474 [11572] WARN - NAT: UPnP, error unmapping port 11394, error: The specified value does not exist in the array.
Oct 18, 2018 13:25:36.725 [11572] WARN - NAT: PMP, got an error: NATPMP_ERR_RECVFROM.
This implies that the port forward for 11394 was not in the router - when it was re-established 36 minutes before
Oct 18, 2018 12:49:20.739 [13452] DEBUG - PublicAddressManager: Got public IP from http://plex.tv: 72.xxx.xxx.xxx
Oct 18, 2018 12:49:23.719 [14572] DEBUG - NAT: UPnP, mapped port 11394 to 192.168.1.153:32400.
Oct 18, 2018 12:49:23.759 [13452] DEBUG - NAT: UPnP, public address is 72.xxx.xxx.xxx
Oct 18, 2018 12:49:23.771 [14572] DEBUG - PublicAddressManager: Mapping succeeded for 192.168.1.153:11394.
The next time there was an issue was 00:15 on 19 Oct when the route through that public port failed
Oct 19, 2018 00:15:02.263 [15908] DEBUG - EventSource: Got event [data] '<Message address="72.xxx.xxx.xxx" port="11394" asyncIdentifier="76646be4-2a57-4e09-a2c9-5de90cb4e0aa" connectivity="0" command="notifyConnectivity"/>'
Oct 19, 2018 00:15:07.692 [15908] DEBUG - EventSource: Got event [data] '<Message address="72.xxx.xxx.xxx" port="11394" asyncIdentifier="4c71a915-ff1f-4a1c-8fd2-6c73c4a82b4b" connectivity="0" command="notifyConnectivity"/>'
Again when you disabled remote access, PMS got an error from the router when attempting to delete that port mapping
Oct 19, 2018 00:15:26.950 [5300] WARN - NAT: UPnP, error unmapping port 11394, error: The specified value does not exist in the array.
As if it disappeared from the router
What router is it ? May be there is an issue with some firmware update - there was reported recently for an ARRIS router
You should find switching to a manually specified port and a port forward to be more reliable than the uPnP auto mapping