I don't know about Canonical, but Red Hat at least recommend reinstalling over in-place upgrades too.

Because you can upgrade from windows 3.11 all the way to 10, good luck with ubuntu.

Yeah, I see your point.

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.

> Because you can upgrade from windows 3.11 all the way to 10

That has never ever worked for me until the 7 -> 10 upgrade: 95 -> 98, 98 -> 2k, 2k -> XP and XP -> 7 all failed miserably and required installing from scratch.

And even 7 -> 10 failed without any helpful information= the first few times I tried it (unlike OSX where I've been upgrading and migrating the same system for more than 10 years across multiple machines and versions).

This is more like 7 -> 10 (14.04 is LTS predecessor to 16.04). Totally valid upgrade path.

There are people who have done it all of the way from Windows 1.