@nuclear_monkey said:
Unfortunately, I didn’t have the server set to generate a log file before I lost access to its settings. Is there any file I can modify without using the web interface to get the server to generate a log?
No - it generates a log anyway unless it crashes out or there is permissions issue. The setting is only to increase level of logging - but there should be log files anyway regardless of logging level
Starting Plex Media Server in terminal session would identify startup errors and if it crashes
cd /Applications
./Plex\ Media\ Server.app/Contents/MacOS/Plex\ Media\ Server
