I am not seeing crashes but there is some evidence that suggests you have two instances of Plex Media Server.exe running at some point - perhaps one as a service or scheduled task and the other the normal auto launch on login / start of windows session
The logs show some overlap - which suggests two parallel Plex Media Server.exe processes running
.5 Jun 09, 2019 06:17:49.638 to Jun 09, 2019 09:22:30.990
.4 Jun 09, 2019 09:22:30.997 to Jun 09, 2019 11:28:27.210
.2 Jun 09, 2019 11:28:27.216 to Jun 09, 2019 13:28:06.428
.3 Jun 09, 2019 10:53:27.501 to Jun 10, 2019 07:14:30.947
.1 Jun 10, 2019 07:14:30.955 to Jun 10, 2019 13:16:07.472
Jun 10, 2019 13:17:28.484 to Jun 10, 2019 13:44:36.274
Also the presence of warnings such as these periodically logged is indicative of the process running as a service or scheduled task
Jun 09, 2019 11:28:36.175 [2216] WARN - Shell_NotifyIcon(NIM_ADD) failed: 0x80004005
Jun 09, 2019 11:28:41.171 [2216] WARN - Shell_NotifyIcon(NIM_ADD) failed: 0x80004005
If you intend to run it as service/scheduled task, you must disable the auto start of Plex Media Server on login / boot
You should delete
HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\Run\Plex Media Server
You would be better off using the solution that many users have adopted rather than do it yourself
See PMS as a service
