Have you looked at snapcast? It's one of the tools I'm going to evaluate for a similar use case. I'm not sure if it works with Plex OOTB but it the docs say it supports UPnP. Snapcast is actively maintained so you can just create an issue on github and see how they reply.
This looks like a good shout. I have actually tried it out but it was years ago when I was trying to get a Sonos-like service and ultimately settled on Squeezebox.
Maybe it's time to try it again, thanks for the idea
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