To accomplish what I have described above requires Plex to run as a service in Windows. The server updates and reboots automatically, and after each update, Plex Media Server automatically restarts so Plex is available as long as the system is running. I run the machine headless, which means there is no monitor attached to it, and I also don't have a user logged into the machine unless I need to perform some maintenance. My Plex server is currently running on a Windows 10 workstation that I keep under my desk.
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