Logs folder… Easy enough. Geez. 
Here is the application log (just for the current session) from my iMac:
Jul 06, 2018 21:00:33.044 INFO - Starting app...
Jul 06, 2018 21:00:38.902 DEBUG - Window bounds is 23 x 47.
Jul 06, 2018 21:00:40.085 INFO - Adding key mapping: MediaNextTrack -> next
Jul 06, 2018 21:00:40.203 INFO - Adding key mapping: MediaPlayPause -> playpause
Jul 06, 2018 21:00:40.203 INFO - Adding key mapping: MediaPreviousTrack -> previous
Jul 06, 2018 21:00:40.203 INFO - Adding key mapping: Shift+CommandOrControl+Space -> activate
Jul 06, 2018 21:00:40.235 INFO - Adding key mapping: Shift+Command+Control+Option+0 -> unrate
Jul 06, 2018 21:00:40.236 INFO - Adding key mapping: Shift+Command+Control+Option+1 -> rate1
Jul 06, 2018 21:00:40.236 INFO - Adding key mapping: Shift+Command+Control+Option+2 -> rate2
Jul 06, 2018 21:00:40.236 INFO - Adding key mapping: Shift+Command+Control+Option+3 -> rate3
Jul 06, 2018 21:00:40.236 INFO - Adding key mapping: Shift+Command+Control+Option+4 -> rate4
Jul 06, 2018 21:00:40.237 INFO - Adding key mapping: Shift+Command+Control+Option+5 -> rate5
Jul 06, 2018 21:00:40.237 INFO - Adding key mapping: Shift+CommandOrControl+Option+Right -> nextalbum
Jul 06, 2018 21:00:40.238 INFO - Adding key mapping: CommandOrControl+Option+Up -> volumeup
Jul 06, 2018 21:00:40.238 INFO - Adding key mapping: CommandOrControl+Option+Down -> volumedown
Jul 06, 2018 21:00:40.239 DEBUG - UPDATES: Using latest channel.
Jul 06, 2018 21:00:40.455 INFO - Checking for update
Jul 06, 2018 21:00:42.169 INFO - Update for version 1.0.5 is not available (latest version: 1.0.5, downgrade is disallowed.
Jul 06, 2018 21:00:42.169 DEBUG - Autoupdate: Update is not available.
Jul 06, 2018 21:00:43.734 INFO - METRICS: Initializing.
Jul 06, 2018 21:00:43.735 INFO - ACCOUNT: Refreshing data.
Jul 06, 2018 21:00:43.735 INFO - DEVICE: Initializing manager.
Jul 06, 2018 21:00:43.736 INFO - DEVICE: Fetching latest provider list from cloud.
Jul 06, 2018 21:00:43.737 INFO - DEVICE: Fetching latest list from cloud.
Jul 06, 2018 21:00:43.737 INFO - DEVICE: Starting connection test.
Jul 06, 2018 21:00:43.738 INFO - DEVICE: Finding best connection for Forker/Trapp Plex
Jul 06, 2018 21:00:43.738 INFO - HTTP: Issuing request to https://127.0.0.1:32400/
Jul 06, 2018 21:00:43.739 INFO - HTTP: Issuing request to https://192.168.7.211:32400/
Jul 06, 2018 21:00:43.739 INFO - HTTP: Issuing request to https://172.17.0.1:32400/
Jul 06, 2018 21:00:43.739 INFO - HTTP: Issuing request to https://XXX.XXX.XXX.XXX:19150/
Jul 06, 2018 21:00:44.113 WARN - DEVICE: Server connection https://127.0.0.1:32400 didn't work for Forker/Trapp Plex: connect ECONNREFUSED 127.0.0.1:32400
Jul 06, 2018 21:00:44.326 INFO - HTTP: Issuing request to https://192.168.7.211:32400/hubs/sections/12?count=4&includeLibraryPlaylists=1&includeStations=1&excludeFields=summary
Jul 06, 2018 21:00:44.640 INFO - DEVICE: Server connection worked for Forker/Trapp Plex ~ https://73.146.214.172:19150
Jul 06, 2018 21:00:44.640 INFO - HTTP: Issuing request to https://73.146.214.172:19150/library/sections
Jul 06, 2018 21:00:44.643 INFO - DEVICE: Server connection worked for Forker/Trapp Plex ~ https://192.168.7.211:32400
Jul 06, 2018 21:00:44.643 INFO - DEVICE: Updating with better local connection.
Jul 06, 2018 21:00:44.650 INFO - Another new request came in, tossing data (looking for: 1, was: 2)
Jul 06, 2018 21:00:45.701 INFO - METRICS: Saving latest cloud settings for metrics.
Jul 06, 2018 21:00:45.719 INFO - DEVICE: Fetched 6 devices from the cloud.
Jul 06, 2018 21:00:45.776 INFO - DEVICE: 7 libraries at Forker/Trapp Plex: DVR,Home Videos,Movies,Music,Photos,Photos (New),TV Shows
Jul 06, 2018 21:00:45.776 INFO - DEVICE: Fast-path connection testing.
Jul 06, 2018 21:00:45.777 INFO - DEVICE: Finding best connection for Neil’s iPhone 7 Plus
Jul 06, 2018 21:00:45.777 INFO - HTTP: Issuing request to http://192.168.7.47:32500/resources
Jul 06, 2018 21:00:45.777 INFO - DEVICE: Finding best connection for Outside
Jul 06, 2018 21:00:45.777 INFO - HTTP: Issuing request to http://172.17.0.2:20000/resources
Jul 06, 2018 21:00:45.778 INFO - DEVICE: Finding best connection for Neil’s iPad Pro
Jul 06, 2018 21:00:45.778 INFO - HTTP: Issuing request to http://192.168.7.24:32500/resources
Jul 06, 2018 21:00:45.778 INFO - DEVICE: Persisting devices.
Jul 06, 2018 21:00:45.778 INFO - DEVICE: Initialization finished in 2032ms.
Jul 06, 2018 21:00:46.018 INFO - APP: Refreshing player/server menu.
Jul 06, 2018 21:00:46.100 WARN - DEVICE: Player connection http://192.168.7.24:32500 didn't work for Neil’s iPad Pro: connect ECONNREFUSED 192.168.7.24:32500
Jul 06, 2018 21:00:46.101 WARN - DEVICE: Connection testing failed for Neil’s iPad Pro
Jul 06, 2018 21:00:46.101 WARN - DEVICE: Player connection http://192.168.7.47:32500 didn't work for Neil’s iPhone 7 Plus: connect ECONNREFUSED 192.168.7.47:32500
Jul 06, 2018 21:00:46.101 WARN - DEVICE: Connection testing failed for Neil’s iPhone 7 Plus
Jul 06, 2018 21:00:48.795 WARN - DEVICE: Server connection https://172.17.0.1:32400 didn't work for Forker/Trapp Plex: timeout of 5000ms exceeded
Jul 06, 2018 21:00:50.767 WARN - DEVICE: Player connection http://172.17.0.2:20000 didn't work for Outside: timeout of 5000ms exceeded
Jul 06, 2018 21:00:50.767 WARN - DEVICE: Connection testing failed for Outside
Jul 06, 2018 21:00:50.768 INFO - APP: Refreshing player/server menu.
Jul 06, 2018 21:01:04.938 ERROR - PLAYER: Error issuing request to player Local: /player/timeline/poll?wait=1&includeMetadata=1&commandID=4&type=audio socket hang up
And here is the server log…
Jul 06, 2018 21:00:33 DEBUG - DEVICE: Loaded 6 devices.
Jul 06, 2018 21:00:33 INFO - [PUBSUB] Connecting...
Jul 06, 2018 21:00:34 DEBUG - CODEC: Checking for device identifier in /Users/neil/Library/Application Support/Plexamp/Codecs/.device-id
Jul 06, 2018 21:00:34 DEBUG - CODEC: Read db852974-a7e8-4e70-9f85-60eb7fd826ed
Jul 06, 2018 21:00:34 DEBUG - CODEC: Initialize complete.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Initializing manager.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Fetching latest provider list from cloud.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Fetching latest list from cloud.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Starting connection test.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Finding best connection for Forker/Trapp Plex
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to https://127.0.0.1:32400/
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to https://192.168.7.211:32400/
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to https://172.17.0.1:32400/
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to https://XXX.XXX.XXX.XXX:19150/
Jul 06, 2018 21:00:34 INFO - [MPD] Started, now we will connect
Jul 06, 2018 21:00:34 INFO - [MPD] Connecting...
Jul 06, 2018 21:00:34 WARN - DEVICE: Server connection https://127.0.0.1:32400 didn't work for Forker/Trapp Plex: connect ECONNREFUSED 127.0.0.1:32400
Jul 06, 2018 21:00:34 ERROR - [MPD] Error connecting:Error: connect ECONNREFUSED 127.0.0.1:36600
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Server connection worked for Forker/Trapp Plex ~ https://192.168.7.211:32400
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to https://192.168.7.211:32400/library/sections
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Server connection worked for Forker/Trapp Plex ~ https://73.146.214.172:19150
Jul 06, 2018 21:00:34 INFO - [MPD] Connecting...
Jul 06, 2018 21:00:34 ERROR - [MPD] Error connecting:Error: connect ECONNREFUSED 127.0.0.1:36600
Jul 06, 2018 21:00:34 DEBUG - DEVICE: 7 libraries at Forker/Trapp Plex: DVR,Home Videos,Movies,Music,Photos,Photos (New),TV Shows
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Fast-path connection testing.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Finding best connection for Neil’s iPhone 7 Plus
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to http://192.168.7.47:32500/resources
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Finding best connection for Outside
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to http://172.17.0.2:20000/resources
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Finding best connection for Neil’s iPad Pro
Jul 06, 2018 21:00:34 DEBUG - HTTP: Issuing request to http://192.168.7.24:32500/resources
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Persisting devices.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Initialization finished in 219ms.
Jul 06, 2018 21:00:34 WARN - DEVICE: Player connection http://192.168.7.24:32500 didn't work for Neil’s iPad Pro: connect ECONNREFUSED 192.168.7.24:32500
Jul 06, 2018 21:00:34 WARN - DEVICE: Connection testing failed for Neil’s iPad Pro
Jul 06, 2018 21:00:34 WARN - DEVICE: Player connection http://192.168.7.47:32500 didn't work for Neil’s iPhone 7 Plus: connect ECONNREFUSED 192.168.7.47:32500
Jul 06, 2018 21:00:34 WARN - DEVICE: Connection testing failed for Neil’s iPhone 7 Plus
Jul 06, 2018 21:00:34 INFO - [MPD] Connecting...
Jul 06, 2018 21:00:34 ERROR - [MPD] Error connecting:Error: connect ECONNREFUSED 127.0.0.1:36600
Jul 06, 2018 21:00:34 INFO - [MPD] Connecting...
Jul 06, 2018 21:00:34 INFO - [CLOUD] Registered device.
Jul 06, 2018 21:00:34 INFO - [PUBSUB] Connected.
Jul 06, 2018 21:00:34 DEBUG - DEVICE: Fetched 6 devices from the cloud.
Jul 06, 2018 21:00:36 INFO - [MPD] Ready!
Jul 06, 2018 21:00:36 DEBUG - [MPD] Not restoring a play queue.
Jul 06, 2018 21:00:36 DEBUG - METRICS: Initializing.
Jul 06, 2018 21:00:36 INFO - [EXPRESS] Listening on port 36000
Jul 06, 2018 21:00:36 DEBUG - METRICS: Saving latest cloud settings for metrics.
Jul 06, 2018 21:00:39 WARN - DEVICE: Server connection https://172.17.0.1:32400 didn't work for Forker/Trapp Plex: timeout of 5000ms exceeded
Jul 06, 2018 21:00:39 WARN - DEVICE: Player connection http://172.17.0.2:20000 didn't work for Outside: timeout of 5000ms exceeded
Jul 06, 2018 21:00:39 WARN - DEVICE: Connection testing failed for Outside
Jul 06, 2018 21:00:48 DEBUG - DEVICE: Persisting devices because Forker/Trapp Plex was dirty.
Jul 06, 2018 21:00:48 DEBUG - DEVICE: Persisting devices.
So, key from the server log is this…?
Jul 06, 2018 21:00:39 WARN - DEVICE: Connection testing failed for Outside