@nickewi - it is not very clear from the logs and it may not be a Plex Media Server issue. Could even be a network / router issue. Will keep an open mind
I will go through the specifics
I can only 08:30 am CST time in the logs - no 8:30pm. Logs cover
Nov 18, 2020 00:36:27 to Nov 18, 2020 10:59:04 and then
Nov 18, 2020 11:00:19 to Nov 18, 2020 11:09:51 when the logs were captured
I can see Plex Tuner Service process exiting with exit code DBG_TERMINATE_PROCESS (x 40010004) at Nov 18, 2020 10:59:04 but that was probably from you shutting down rather than indicative of an error.
There is evidence of memory allocation failure but that was many hours before and would not expect it to be relevant
Nov 18, 2020 02:10:07.947 [7800] ERROR - Butler: Uncaught exception running subtask ButlerTaskGenerateIntroMarkers: bad allocation
The last activity in the log before you shutdown and restarted at 10:59:04 was
at 10:47:53 you editing server settings for max WAN upload set at 8000
Android Device AFTEAMR311 on local IP 192.168.0.39 sending indication that playback was paused for ‘Misled & Misguided’ - this was at 10:45:32
Device on 192.168.0.255 was direct playing Road House movie - this was Plex Web Google Chrome
Communication from those two devices stopped around 10:45 / 10:46 = but server was still running until restart at 10:59
playback on the server directly in Plex Web via loopback 127.0.0.1 continued
This suggests that there may have been a network issue
Nov 18, 2020 10:45:46.169 [9724] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 21.964047 seconds: 192.168.0.1 (OnHub)
Nov 18, 2020 10:45:46.169 [9724] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 21.964047 seconds: 192.168.0.1 (WANDevice)
Nov 18, 2020 10:45:46.169 [9724] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 21.964047 seconds: 192.168.0.1 (WANConnectionDevice)
Nov 18, 2020 10:45:46.169 [9724] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 20.672757 seconds: 192.168.0.26 (LaneyRoom)
Nov 18, 2020 10:45:46.169 [9724] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 20.422701 seconds: 192.168.0.36 (HDHomeRun DMS 10754F44)
Also attempt to communicate with one of the DVRs failed when it was ok before
Nov 18, 2020 10:45:46.170 [11188] DEBUG - Grabber: HDHomerun discovered a model HDTC-2US.
Nov 18, 2020 10:45:46.170 [11188] DEBUG - HTTP requesting GET http://192.168.0.35:80/discover.json
Nov 18, 2020 10:45:51.181 [11188] ERROR - Error issuing curl_easy_perform(handle): 28
Nov 18, 2020 10:45:51.181 [11188] DEBUG - HTTP simulating 408 after curl timeout
For the 21st November logs, last request from the apple device tvOS (Living Room) was at 22:31:33
This type of request is periodic and for the apple device it is sent every 5 seconds - as can be seen here
Nov 21, 2020 22:31:22.883 [2480] DEBUG - Request: [192.168.0.244:62599 (Subnet)] GET /:/timeline?bufferedTime=77&duration=2520384&key=%2Flibrary%2Fmetadata%2F45768&location=lan&playQueueItemID=13788&playbackTime=2195773&ratingKey=45768&state=playing&time=2195668 (13 live) TLS GZIP Signed-in Token (nickewi)
Nov 21, 2020 22:31:22.886 [15732] DEBUG - Completed: [192.168.0.244:62599] 200 GET /:/timeline?bufferedTime=77&duration=2520384&key=%2Flibrary%2Fmetadata%2F45768&location=lan&playQueueItemID=13788&playbackTime=2195773&ratingKey=45768&state=playing&time=2195668 (13 live) TLS GZIP 3ms 776 bytes (pipelined: 105)
Nov 21, 2020 22:31:27.886 [2480] DEBUG - Request: [192.168.0.244:62599 (Subnet)] GET /:/timeline?bufferedTime=72&duration=2520384&key=%2Flibrary%2Fmetadata%2F45768&location=lan&playQueueItemID=13788&playbackTime=2200773&ratingKey=45768&state=playing&time=2200668 (13 live) TLS GZIP Signed-in Token (nickewi)
Nov 21, 2020 22:31:27.890 [15732] DEBUG - Completed: [192.168.0.244:62599] 200 GET /:/timeline?bufferedTime=72&duration=2520384&key=%2Flibrary%2Fmetadata%2F45768&location=lan&playQueueItemID=13788&playbackTime=2200773&ratingKey=45768&state=playing&time=2200668 (13 live) TLS GZIP 3ms 775 bytes (pipelined: 108)
Nov 21, 2020 22:31:33.659 [8372] DEBUG - Request: [192.168.0.244:62599 (Subnet)] GET /:/timeline?bufferedTime=67&duration=2520384&key=%2Flibrary%2Fmetadata%2F45768&location=lan&playQueueItemID=13788&playbackTime=2205804&ratingKey=45768&state=playing&time=2205701 (16 live) TLS GZIP Signed-in Token (nickewi)
Nov 21, 2020 22:31:33.663 [15728] DEBUG - Completed: [192.168.0.244:62599] 200 GET /:/timeline?bufferedTime=67&duration=2520384&key=%2Flibrary%2Fmetadata%2F45768&location=lan&playQueueItemID=13788&playbackTime=2205804&ratingKey=45768&state=playing&time=2205701 (16 live) TLS GZIP 3ms 776 bytes (pipelined: 109)
and they stopped coming in
Again we have an indication of a network issue / router failing
Nov 21, 2020 22:31:50.256 [2648] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 21.946427 seconds: 192.168.0.1 (OnHub)
Nov 21, 2020 22:31:50.256 [2648] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 21.946427 seconds: 192.168.0.1 (WANDevice)
Nov 21, 2020 22:31:50.256 [2648] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 21.946427 seconds: 192.168.0.1 (WANConnectionDevice)
Nov 21, 2020 22:32:00.267 [10936] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 28.118810 seconds: 192.168.0.26 (LaneyRoom)
Nov 21, 2020 22:32:00.267 [10936] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 29.599142 seconds: 192.168.0.35 (HDHomeRun DMS 10559557)
Nov 21, 2020 22:32:00.267 [10936] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 29.517123 seconds: 192.168.0.36 (HDHomeRun DMS 10754F44)
Nov 21, 2020 22:32:00.267 [10936] DEBUG - NetworkServiceBrowser: SSDP departed after not being seen for 28.802963 seconds: 192.168.0.37 ([LG] webOS TV UH6035)
I suggest investigating at the router / network end - there is no evidence of any deadlocks in the Plex Media Server process as local requests through 127.0.0.1 were being processed