Yeah, it's rough. Things are always easier said that done.
We know risks. Unfortunately, we work in a 24/7 enterpries with so many servers and services.
As I wrote, we have a team that has been upgrading 2008 servers for a few years. We're still not done.
we have 150 DCs, 70 DHCP servers, so many SQL servers and IIS servers. I don't know the number. Apps and services for so many internal tools. It's a lot.

If I worked in a small environment with a couple hundred servers, it would be so easy.
Unfortunately, that's not what I have.

I've worked at my company in this role for 17 of the last 20 years and we've never had anything like this happen regardless of how stupid you may think we are. Maybe we were lulled to sleep, but I really think we're just too slow.