Config and media library lost after ever Windows server reboot

Server Version#:
Player Version#:
I am asked to “claim” the server again every time. It is extremely frustrating as I lose all the data I’ve entered in my library.

That doesn’t sound right. Plex Media Server should be saving your Plex info into the user’s registry so it should remember the next time. Possibilities are:
1 - You are signing into Windows with a different user so there are no registry entries
2 - Your registry is not being saved. Are you using an admin account? If you are using a restricted user account, then that could prevent the registry from being saved, so all the settings only exist until that user logs out.