Transcoder Dev is saying the error showing error number -138 is a windows error for a timeout on the request. We discussed getting a set of verbose logs to see if there is any additional information. Before we try that it would be nice to eliminate all the messages coming from the scanning of your photos. If you’re not using photos could you possibly remove the library from Plex that way it stops the scanning or rename the top-level folder on your drive the photos are stored in so Plex quits trying to scan them all the time?
The other thing I have noticed in the logs is numerous slow query messages, these were just the 16:33 messages:
Sep 10, 2020 16:33:00.325 [16904] WARN - SLOW QUERY: It took 203.125000 ms to retrieve 16 items.
Sep 10, 2020 16:33:00.346 [10556] WARN - SLOW QUERY: It took 375.000000 ms to retrieve 50 items.
Sep 10, 2020 16:33:05.309 [16036] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 10 items.
Sep 10, 2020 16:33:05.319 [10556] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 16 items.
Sep 10, 2020 16:33:05.329 [4220] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 31 items.
Sep 10, 2020 16:33:05.330 [4604] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 31 items.
Sep 10, 2020 16:33:05.362 [16904] WARN - SLOW QUERY: It took 234.375000 ms to retrieve 31 items.
Sep 10, 2020 16:33:05.368 [7912] WARN - SLOW QUERY: It took 234.375000 ms to retrieve 50 items.
Sep 10, 2020 16:33:05.397 [4516] WARN - SLOW QUERY: It took 203.125000 ms to retrieve 50 items.
Sep 10, 2020 16:33:10.282 [4516] WARN - SLOW QUERY: It took 218.750000 ms to retrieve 16 items.
Sep 10, 2020 16:33:10.312 [18320] WARN - SLOW QUERY: It took 312.500000 ms to retrieve 16 items.
Sep 10, 2020 16:33:10.341 [7912] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 31 items.
Sep 10, 2020 16:33:10.374 [10556] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 31 items.
Sep 10, 2020 16:33:10.375 [4604] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 31 items.
Sep 10, 2020 16:33:10.387 [16036] WARN - SLOW QUERY: It took 375.000000 ms to retrieve 50 items.
Sep 10, 2020 16:33:15.326 [16916] WARN - SLOW QUERY: It took 234.375000 ms to retrieve 16 items.
Sep 10, 2020 16:33:15.397 [16036] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 50 items.
Sep 10, 2020 16:33:20.295 [13540] WARN - SLOW QUERY: It took 203.125000 ms to retrieve 16 items.
Sep 10, 2020 16:33:20.341 [16916] WARN - SLOW QUERY: It took 312.500000 ms to retrieve 10 items.
Sep 10, 2020 16:33:20.357 [16036] WARN - SLOW QUERY: It took 468.750000 ms to retrieve 16 items.
Sep 10, 2020 16:33:20.360 [4516] WARN - SLOW QUERY: It took 296.875000 ms to retrieve 31 items.
Sep 10, 2020 16:33:20.362 [7912] WARN - SLOW QUERY: It took 296.875000 ms to retrieve 31 items.
Sep 10, 2020 16:33:20.397 [18320] WARN - SLOW QUERY: It took 406.250000 ms to retrieve 50 items.
Sep 10, 2020 16:33:25.309 [4220] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 16 items.
Sep 10, 2020 16:33:25.328 [13540] WARN - SLOW QUERY: It took 281.250000 ms to retrieve 16 items.
Sep 10, 2020 16:33:25.899 [18296] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 16 items.
Sep 10, 2020 16:33:25.935 [4604] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 31 items.
Sep 10, 2020 16:33:26.024 [7912] WARN - SLOW QUERY: It took 203.125000 ms to retrieve 50 items.
Sep 10, 2020 16:33:30.050 [18320] WARN - SLOW QUERY: It took 234.375000 ms to retrieve 50 items.
Sep 10, 2020 16:33:31.856 [5024] WARN - SLOW QUERY: It took 250.000000 ms to retrieve 50 items.
Sep 10, 2020 16:33:42.861 [16036] WARN - SLOW QUERY: It took 203.125000 ms to retrieve 16 items.
Sep 10, 2020 16:33:54.077 [12504] WARN - SLOW QUERY: It took 312.500000 ms to retrieve 16 items.
Sep 10, 2020 16:33:54.141 [16036] WARN - SLOW QUERY: It took 406.250000 ms to retrieve 31 items.
Sep 10, 2020 16:33:54.143 [4516] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 31 items.
Sep 10, 2020 16:33:54.145 [18296] WARN - SLOW QUERY: It took 406.250000 ms to retrieve 50 items.
Sep 10, 2020 16:33:54.152 [5024] WARN - SLOW QUERY: It took 265.625000 ms to retrieve 16 items.
Sep 10, 2020 16:33:54.171 [4604] WARN - SLOW QUERY: It took 328.125000 ms to retrieve 50 items.
You can try to optimize the database by going to Settings/Troubleshooting and clicking the Optimize Database link.
If you can look at the logs after removing the photos library or changing the top-level folder so Plex is no longer scanning the photos constantly, and optimizing the database to see if you are no longer seeing slow query or photo scanning entries.
If the logs look better then we can try turning on Verbose logging. Once turned on restart Plex Media Server so the Verbose change is active. Then try recording something. If it fails grab the logs immediately after the failure. I noticed you have changed the LogNumFiles setting to 15 so hopefully, that will be enough log files to capture the failure. The Dev did say that verbose might not even indicate why Windows is giving the TimeOut error.