I’ve found some discrepancies in your logs.
It looks as if PMS can’t read some files or those files didn’t make it across with the migration. Notice the pathname is incomplete / invalid.
guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fposters%2Fcom%2Eplexapp%2Eagents%2Eimdb_dfa1710f846e37646046ee28553b00c274b4a578
Jan 27, 2020 02:06:52.264 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://posters/com.plexapp.agents.imdb_dfa1710f846e37646046ee28553b00c274b4a578).
Jan 27, 2020 02:06:52.264 [0x7f8c5effd700] DEBUG - Item 5675 (The Killing Fields) Scanning metadata graphic elements in XML file ""/Info.xml
Jan 27, 2020 02:06:52.266 [0x7f8c20ff9700] DEBUG - HTTP requesting GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_1081a4f842cd2b3b455d3a41b2fb86f506d2e692
Jan 27, 2020 02:06:52.276 [0x7f8c20ff9700] DEBUG - HTTP 500 response from GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_1081a4f842cd2b3b455d3a41b2fb86f506d2e692
Jan 27, 2020 02:06:52.276 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://art/com.plexapp.agents.imdb_1081a4f842cd2b3b455d3a41b2fb86f506d2e692).
Jan 27, 2020 02:06:52.276 [0x7f8c217fa700] DEBUG - HTTP requesting GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_48be99c316f522feb015caf3add53dcef8d75916
Jan 27, 2020 02:06:52.284 [0x7f8c217fa700] DEBUG - HTTP 500 response from GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_48be99c316f522feb015caf3add53dcef8d75916
Jan 27, 2020 02:06:52.285 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://art/com.plexapp.agents.imdb_48be99c316f522feb015caf3add53dcef8d75916).
Jan 27, 2020 02:06:52.285 [0x7f8c20ff9700] DEBUG - HTTP requesting GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_fa69c76e6e5dec61836a74e3314dc9d4224ce50a
Jan 27, 2020 02:06:52.294 [0x7f8c20ff9700] DEBUG - HTTP 500 response from GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_fa69c76e6e5dec61836a74e3314dc9d4224ce50a
Jan 27, 2020 02:06:52.294 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://art/com.plexapp.agents.imdb_fa69c76e6e5dec61836a74e3314dc9d4224ce50a).
Jan 27, 2020 02:06:52.294 [0x7f8c217fa700] DEBUG - HTTP requesting GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_72265ea25f1293b12feeee76f93ebc93d3216f27
Jan 27, 2020 02:06:52.302 [0x7f8c217fa700] DEBUG - HTTP 500 response from GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_72265ea25f1293b12feeee76f93ebc93d3216f27
Jan 27, 2020 02:06:52.303 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://art/com.plexapp.agents.imdb_72265ea25f1293b12feeee76f93ebc93d3216f27).
Jan 27, 2020 02:06:52.303 [0x7f8c20ff9700] DEBUG - HTTP requesting GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_a772a148cfee7952b1cc41692a4950cf415907e9
Jan 27, 2020 02:06:52.312 [0x7f8c20ff9700] DEBUG - HTTP 500 response from GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_a772a148cfee7952b1cc41692a4950cf415907e9
Jan 27, 2020 02:06:52.312 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://art/com.plexapp.agents.imdb_a772a148cfee7952b1cc41692a4950cf415907e9).
Jan 27, 2020 02:06:52.312 [0x7f8c217fa700] DEBUG - HTTP requesting GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_326c75d73f9d278e2c1e9604a3b6b3dd325e3c91
Jan 27, 2020 02:06:52.319 [0x7f8c217fa700] DEBUG - HTTP 500 response from GET http://127.0.0.1:45733/system/agents/media/get?guid=com%2Eplexapp%2Eagents%2Eimdb%3A%2F%2Ftt0087553%3Flang%3Den&mediaType=1&url=metadata%3A%2F%2Fart%2Fcom%2Eplexapp%2Eagents%2Eimdb_326c75d73f9d278e2c1e9604a3b6b3dd325e3c91
Jan 27, 2020 02:06:52.319 [0x7f8c5effd700] ERROR - Error bringing media local (metadata://art/com.plexapp.agents.imdb_326c75d73f9d278e2c1e9604a3b6b3dd325e3c91).
Jan 27, 2020 02:06:52.332 [0x7f8c5effd700] DEBUG - Extras: 1 existing extras.
Jan 27, 2020 02:06:52.332 [0x7f8c5effd700] DEBUG - Extras: Checked extra 'The Kil
The primary problem I see is the communication timeout & failure to connect to plex.tv and remain connected. Since this occurs on a regular interval, what else is happing? DHCP refreshing? Is the server WiFi with the AP sleeping? It’s going to be something trivial.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 172.104.132.7 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 139.162.120.52 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 109.237.24.233 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 139.162.20.120 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 184.105.148.115 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 172.105.97.53 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 184.105.148.116 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 82.94.168.18 failed: Connection timed out.
Jan 27, 2020 02:09:50.905 [0x7f8c851e6700] WARN - PubSubManager: Connection to 45.33.103.230 failed: Connection timed out.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] WARN - PubSubManager: Connection to 45.79.23.169 failed: Connection timed out.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] WARN - PubSubManager: Connection to 172.104.213.234 failed: Connection timed out.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] DEBUG - EventSource: Stopping.
Jan 27, 2020 02:09:50.906 [0x7f8c851e6700] ERROR - EventSource: Retrying in 60 seconds.
Jan 27, 2020 02:10:08.727 [0x7f8c849e5700] DEBUG - EventSource: Failure in IdleTimeout (0 - Success).
Jan 27, 2020 02:10:08.727 [0x7f8c849e5700] ERROR - EventSource: Retrying in 60 seconds.
This looks like networking on the host itself is shutting down.
Jan 27, 2020 02:10:51.208 [0x7f8c851e6700] DEBUG - EventSource: Failure in Connect (113 - No route to host).
Jan 27, 2020 02:10:56.208 [0x7f8c851e6700] DEBUG - EventSource: Stopping.