There is a networking problem here.
PMS (the host) cannot communicate out to Plex.tv
Error 28 is a timeout error meaning it thinks it sent the message but no reply was ever received.
Oct 07, 2019 18:49:10.328 [0x7faeb5292700] DEBUG - NAT: UPnP, usable device <http://192.168.1.1:56688/rootDesc.xml> with private address <192.168.1.29>.
Oct 07, 2019 18:49:10.370 [0x7faeb5292700] WARN - NAT: UPnP, error mapping port 15491, error: The port mapping entry specified conflicts with a mapping assigned previously to another client, controlURL: http://192.168.1.1:56688/ctl/IPConn.
Oct 07, 2019 18:49:10.370 [0x7faeb5292700] DEBUG - NAT: PMP, attempting mapping.
Oct 07, 2019 18:49:10.621 [0x7faeb5292700] WARN - NAT: PMP, got an error: Not Supported by gateway.
Oct 07, 2019 18:49:10.621 [0x7faeb5292700] DEBUG - NAT: UPnP, attempting port mapping.
Oct 07, 2019 18:49:10.655 [0x7faeb5292700] DEBUG - NAT: UPnP, usable device <http://192.168.1.1:56688/rootDesc.xml> with private address <192.168.1.29>.
Oct 07, 2019 18:49:10.700 [0x7faeb5292700] WARN - NAT: UPnP, error mapping port 13367, error: The port mapping entry specified conflicts with a mapping assigned previously to another client, controlURL: http://192.168.1.1:56688/ctl/IPConn.
Oct 07, 2019 18:49:10.700 [0x7faeb5292700] DEBUG - PublicAddressManager: Mapping failed.
Oct 07, 2019 18:49:14.614 [0x7fae867fc700] DEBUG - DVR:Device: Discovering and refreshing all devices.
Oct 07, 2019 18:49:14.614 [0x7fae867fc700] DEBUG - DVR:Grabber: HDHomerun discovered 0 compatible devices.
Oct 07, 2019 18:49:14.615 [0x7fae867fc700] DEBUG - HTTP requesting POST http://127.0.0.1:32600/devices/discover
Oct 07, 2019 18:49:17.032 [0x7fae867fc700] DEBUG - HTTP 200 response from POST http://127.0.0.1:32600/devices/discover
Oct 07, 2019 18:49:19.275 [0x7fae9c9ce700] DEBUG - NetworkServiceBrowser: Parsing SSDP schema for http://192.168.1.29:32469/DeviceDescription.xml
Oct 07, 2019 18:49:19.275 [0x7fae9c9ce700] DEBUG - HTTP requesting GET http://192.168.1.29:32469/DeviceDescription.xml
Oct 07, 2019 18:49:19.279 [0x7fae9c9ce700] DEBUG - HTTP 200 response from GET http://192.168.1.29:32469/DeviceDescription.xml
Oct 07, 2019 18:49:19.279 [0x7fae9c9ce700] DEBUG - NetworkServiceBrowser: found 1 SSDP devices via http://192.168.1.29:32469/DeviceDescription.xml
Oct 07, 2019 18:49:19.280 [0x7fae9c9ce700] DEBUG - NetworkServiceBrowser: SSDP arrived: 192.168.1.29 (Plex Media Server: Media-Server)
Oct 07, 2019 18:49:20.145 [0x7faeb5a93700] ERROR - Error issuing curl_easy_perform(handle): 28
Oct 07, 2019 18:49:20.145 [0x7faeb5a93700] DEBUG - HTTP simulating 408 after curl timeout
Oct 07, 2019 18:49:20.145 [0x7faeb5a93700] ERROR - Error parsing content.
Oct 07, 2019 18:49:20.145 [0x7faeb5a93700] ERROR - Error parsing XML: Error parsing file.
Oct 07, 2019 18:49:22.792 [0x7faeb4a91700] ERROR - Error issuing curl_easy_perform(handle): 28
Oct 07, 2019 18:49:22.792 [0x7faeb4a91700] DEBUG - HTTP simulating 408 after curl timeout
Oct 07, 2019 18:49:22.792 [0x7faeb4a91700] ERROR - PublicAddressManager: Unable to get public IP adddress from myPlex (httpCode=408):
Oct 07, 2019 18:49:22.805 [0x7fae86ffd700] ERROR - Error issuing curl_easy_perform(handle): 28
Oct 07, 2019 18:49:22.805 [0x7fae7ffff700] ERROR - Error issuing curl_easy_perform(handle): 28
Oct 07, 2019 18:49:22.806 [0x7fae86ffd700] DEBUG - HTTP simulating 408 after curl timeout
Oct 07, 2019 18:49:22.806 [0x7fae86ffd700] ERROR - AutoTagging: unable to retrieve updated word lists
Oct 07, 2019 18:49:22.806 [0x7fae7ffff700] DEBUG - HTTP simulating 408 after curl timeout
Oct 07, 2019 18:49:22.806 [0x7fae7ffff700] WARN - [Analytics] Couldn't get analytics privacy settings. Trying again soon.
Oct 07, 2019 18:49:22.806 [0x7fae7ffff700] DEBUG - Running database fix-ups.
Oct 07, 2019 18:49:22.807 [0x7fae7ffff700] DEBUG - Database Fixups: Destroyed 0 transient items.
Oct 07, 2019 18:49:22.809 [0x7fae7ffff700] DEBUG - Running database fix-ups completed in 0.0 seconds.
Oct 07, 2019 18:49:22.810 [0x7fae7ffff700] DEBUG - HTTP requesting GET https://plex.tv/api/v2/features?X-Plex-Token=
Oct 07, 2019 18:49:25.806 [0x7fae877fe700] WARN - [Analytics] Attempting to send unrecognized metric (server:startup). Skipping.
Oct 07, 2019 18:49:38.335 [0x7fae7ffff700] ERROR - Error issuing curl_easy_perform(handle): 28
Oct 07, 2019 18:49:38.335 [0x7fae7ffff700] DEBUG - HTTP simulating 408 after curl timeout
Oct 07, 2019 18:49:38.335 [0x7fae7ffff700] WARN - FeatureManager: Couldn't get features. Trying again soon.
Oct 07, 2019 18:49:38.336 [0x7fae85ffb700] DEBUG - DVR: Starting up.
Oct 07, 2019 18:49:38.337 [0x7fae85ffb700] DEBUG - Activity: registered new activity