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Hey Guys, how do you manage WordPress plugin update across multiple instances so you make sure that the new version is compatible with the current setup and WordPress core version, and same issue for the core WordPress update as well? How to do that not ending up with WSOD? Thanks!

You do that by using well known, well supported plugins.
I maintain around ~120 sites and run updates (via ManageWP) 3-4 times a week – zero problems since I’ve been doing this in the last 12+ years.
Nightly backups and UptimeRobot for peace of mind.