Yes I’m seeing crashes.
The main functions in Plex are broken up into plug-in bundles.
Below is what I see when starting my server vs what I saw from your log.
Every time your log says the System bundle was restarted, it crashed.
So it’s never making it’s log file, com.plexapp.system.log
In my server log
Oct 16, 2019 10:11:39.853 [0x7f0d92b7d700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/System.bundle.
Oct 16, 2019 10:11:46.560 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/LocalMedia.bundle.
Oct 16, 2019 10:11:46.560 [0x7f0d90e31700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/Scanners.bundle.
Oct 16, 2019 10:11:46.560 [0x7f0d90b43700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/Musicbrainz.bundle.
Oct 16, 2019 10:11:46.561 [0x7f0d90e31700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/WebClient.bundle.
Oct 16, 2019 10:11:46.565 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/MoviePosterDB.bundle.
Oct 16, 2019 10:11:46.565 [0x7f0d90e31700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/OpenSubtitles.bundle.
Oct 16, 2019 10:11:46.568 [0x7f0d90b43700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/LyricFind.bundle.
Oct 16, 2019 10:11:46.568 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/PlexThemeMusic.bundle.
Oct 16, 2019 10:11:46.569 [0x7f0d90e31700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/LastFM.bundle.
Oct 16, 2019 10:11:46.570 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/PlexMovie.bundle.
Oct 16, 2019 10:11:46.570 [0x7f0d90b43700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/Framework.bundle.
Oct 16, 2019 10:11:46.571 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/TheTVDB.bundle.
Oct 16, 2019 10:11:46.572 [0x7f0d90b43700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/PersonalMedia.bundle.
Oct 16, 2019 10:11:46.571 [0x7f0d90e31700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/PlexMusic.bundle.
Oct 16, 2019 10:11:46.573 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/HTbackdrops.bundle.
Oct 16, 2019 10:11:46.574 [0x7f0d90b43700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/Media-Flags.bundle.
Oct 16, 2019 10:11:46.575 [0x7f0d90b43700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/TheMovieDB.bundle.
Oct 16, 2019 10:11:46.575 [0x7f0d90855700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Resources/Plug-ins-10fc2f8d3/Fanart-TV.bundle.
Oct 16, 2019 10:11:46.576 [0x7f0d90e31700] DEBUG - Starting plug-in /share/CACHEDEV1_DATA/.qpkg/PlexMediaServer/Library/Plex Media Server/Plug-ins/Services.bundle.
and in your log
Oct 16, 2019 17:53:27.030 [0x7fa48effd700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/System.bundle.
Oct 16, 2019 17:53:27.507 [0x7fa48effd700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:27.508 [0x7fa44effd700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/Fanart-TV.bundle.
Oct 16, 2019 17:53:27.508 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/Framework.bundle.
Oct 16, 2019 17:53:27.508 [0x7fa44dffb700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/HTbackdrops.bundle.
Oct 16, 2019 17:53:27.508 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/LastFM.bundle.
Oct 16, 2019 17:53:27.757 [0x7fa44effd700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/LocalMedia.bundle.
Oct 16, 2019 17:53:27.757 [0x7fa44dffb700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/LyricFind.bundle.
Oct 16, 2019 17:53:27.758 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/Media-Flags.bundle.
Oct 16, 2019 17:53:27.758 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/MoviePosterDB.bundle.
Oct 16, 2019 17:53:28.011 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/Musicbrainz.bundle.
Oct 16, 2019 17:53:28.018 [0x7fa44dffb700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/OpenSubtitles.bundle.
Oct 16, 2019 17:53:28.021 [0x7fa484ff9700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:28.022 [0x7fa44effd700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/PersonalMedia.bundle.
Oct 16, 2019 17:53:28.268 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/PlexMovie.bundle.
Oct 16, 2019 17:53:28.278 [0x7fa44effd700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/PlexMusic.bundle.
Oct 16, 2019 17:53:28.279 [0x7fa429ffb700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:28.283 [0x7fa44dffb700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/PlexThemeMusic.bundle.
Oct 16, 2019 17:53:28.533 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/Scanners.bundle.
Oct 16, 2019 17:53:28.533 [0x7fa42b7fe700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:28.533 [0x7fa44e7fc700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/TheMovieDB.bundle.
Oct 16, 2019 17:53:28.540 [0x7fa44effd700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/TheTVDB.bundle.
Oct 16, 2019 17:53:28.550 [0x7fa44dffb700] DEBUG - Starting plug-in /usr/lib/plexmediaserver/Resources/Plug-ins-f2cae8d6b/WebClient.bundle.
Oct 16, 2019 17:53:28.551 [0x7fa44dffb700] DEBUG - Starting plug-in /var/lib/plexmediaserver/Library/Application Support/Plex Media Server/Plug-ins/Services.bundle.
Oct 16, 2019 17:53:28.787 [0x7fa4b37fe700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:29.027 [0x7fa4b1ffb700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:29.271 [0x7fa4b0ff9700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:29.498 [0x7fa4b17fa700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:29.725 [0x7fa4b2ffd700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:29.951 [0x7fa4b3fff700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:30.176 [0x7fa487fff700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:30.400 [0x7fa428ff9700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:30.625 [0x7fa413fff700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:30.849 [0x7fa4c1777700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:31.077 [0x7fa48ffff700] DEBUG - System bundle was restarted, we need to notify other plug-ins
Oct 16, 2019 17:53:32.328 [0x7fa4877fe700] DEBUG - Notifying the system bundle an update to server /system/notify/serverUpdated?host=127.0.0.1
Oct 16, 2019 17:53:32.618 [0x7fa4877fe700] DEBUG - System bundle was restarted, we need to notify other plug-ins
...
Oct 16, 2019 17:53:27.258 [0x7fa48effd700] ERROR - Timeout or error reading status line from plug-in pipe [com.plexapp.system], we're killing it.
Oct 16, 2019 17:53:27.258 [0x7fa48effd700] ERROR - Error received reading configuration for com.plexapp.system
Oct 16, 2019 17:53:27.507 [0x7fa48effd700] ERROR - Timeout or error reading status line from plug-in pipe [com.plexapp.system], we're killing it.
Oct 16, 2019 17:53:27.507 [0x7fa48effd700] ERROR - Error received reading configuration for com.plexapp.system
Given that your server can’t start up well, have you ever tried to uninstall it while preserving your metadata and media?