PMS - Doesn't Start Anymore, Tray Icon Disappears Immediately

Try it this way: Unable to update - #2 by OttoKerner

If after doing the above you miss the web app starting after a computer reboot, or the server is not automatically starting:
start Plex server manually using the regular Windows Start menu
then right-click on the Plex icon in the Windows task tray and enable start at bootup again.