I have actual machines that I was able to flawlessly upgrade from 4.10 to 17.04. Can't say that about Windows. Though I did actually know what I shouldn't mess with if I want the upgrade to go through (or fix before).
You got extremely lucky. Not that windows is much better, but in general there are hiccups to upgrading with most linux distros as well as windows.
I hit problems with the desktop environment on both 8->10 and 10->12, then gave up trying to upgrade Ubuntu in-place. Debian has been absolutely fine, though.