I’ve been running into a similar issue, but it’s more intermittent. Most of the time it works. But sometimes occasionally I’ll log in and try to play something, or try to watch some live TV with HW encoding turned on, and Plex will have crashed. I’ve read a few issues, where Plex as a service can be a problem (which I’m not running as a service) or headless using RDP to access the server.

The question I have, is it only RDP? My crashes happen when RDP isn’t currently active. Would using Teamviewer OR VNC matter?