I will almost guarantee some update will break shit at the most inconvenient time humanly possible and the people you’ve done this for will need your help, all at the same time.
Well, yeah. That's life as an admin under the best circumstances. There's a running list of Windows ticking time bombs over on r/sysadmin. There are lots of good reasons to ditch Windows, but I wouldn't say the risk of MS shutting down technically unsupported hardware is one of them (because I don't agree it's a substantial risk).
It's crazy how on-the-nose The Good Place was with the good guy committee. "It's clear what we need to do: give up all our leverage, and give them whatever they want."