I manage about 150 workstations in a work enviornment, which is not a lot, and I've gotten so tired of the constant need to upgrade our systems. We don't have Win10 Enterprise because of the costs, so we don't get the 30 months of updates on the "09" versions, so every single Windows install we have is only supported for 18 months. I still have about 30 machines on 1803, which goes out of support in November, which means I have until Patch Tuesday in December to get them updated. And then once I have them updated, I'll have to get started on the 50ish machines we have on 1809.
But this is a beacon of light. We've done a pretty big evergreening program in the last few months so I have about 75 computers on 1903, and I'm going to test the upgrade process on a few of them, but I'm not going to have to worry so much about this upgrade, and an just get them onto 1909. That means I'm going to have 75 machines I just don't have to worry about a version update on until at least late 2020, and that's going to give me a breather.
With 150 machines it's not like I spend all of my time doing version updates, but it's a lot more time than it should be, and a lot more time than it used to.