> The point is that you've still done many more distribution upgrades than Windows upgrades in the same timeframe and don't question it.

Which is not the point I was making there. The point was that Windows Upgrades are subjective, whereas when Linux Upgrades are subjective, you can hop to the next OS.

Many end-users have no problem doing even twice as many upgrades, as long as what they're getting isn't worse. And often you're even able to avoid UI changes by making these sidesteps. For example, you could've gone from Ubuntu with GNOME2 to Ubuntu MATE or even Xubuntu and you'd still be using essentially the same UI as you've been able to use since 2002. Program compatibility wouldn't really change then either, it's still Ubuntu, still Linux under the hood.

I also really don't feel like it's fair for you to act like Ubuntu is the only distribution. If you know you want conservative, boring, then you'd install Debian. openSUSE Leap would also be an option, for the most part not quite as conservative as Debian, but at least it's out of its experimenting phase. And if you don't mind monetary costs, then SUSE Linux Enterprise will give you 10 years general support + 3 years extended support.

Lastly, the upgrade isn't just subjective for many companies, it's even likely illegal due to the increased telemetry. Either because they're in a field where by law, they have to abide to user data protection, or because they have contracts that ask for secrecy. And I do think that that is a very legitimate reason to not be upgrading right away or at all. That one, however, is on Microsoft.