Thanks for sharing the log files. I did not see any major problems that would stop you from updating PMS.
When you get your new glasses, please provide a directory listing of your db files. That will show their size.
Also, the next time you restart PMS, please download a new set of log files after Plex fully starts. They will have the Plex’s startup sequence.
Plex Media Server had a problem with the Windows 64-bit version not respecting custom paths when auto updating. I do not know when it first appeared, but it was fixed in 1.40.2. That might have something to do with you having to manually update Plex Media Server.
1.40.2.8273 Release Notes Fixes:
- (Auto Update) Custom install paths are not respected when auto-updating on 64 bit Windows. (PM-1143)