Hi… is there a way to notify the friends that I share my server with of changes/updates i’m performing on my server? For example, have a message appear that states “My Plex server will be down from 1-3 for maintenance this weekend”.
No, that is not possible.
You could install Tautulli and use one of its features to send out a mail or tweet or similar.
I suggest a new tool that has just started to become widely used: email. 
While there have been a smallish number of folks that have mentioned wanting this I think that existing tools outside of Plex performs the needed functionality quite well.
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