I think this is a pretty apples-to-apples comparison: the timeframe in question for Ubuntu has just as many ups and downs as for Windows in terms of upgrades. It includes the Gnome 2 -> Unity -> Gnome 3 transition. The systemd transition is in there somewhere.
That kind of supports my point that if you were sticking to Ubuntu specifically you've seen a lot of change during the support lifetime of Windows 7. No IT department in their right mind would still be running a comparable Linux distribution on user desktops as old as Windows 7, and those Linux distributions have changed nearly as much as Windows 7 through to Windows 10.
Monetary cost is apples-to-oranges and irrelevant to the point I was trying to make, but: the Windows upgrade from 7 and 8.1 to 10 was made free for consumers and small businesses, and Microsoft has aligned with Apple that starting with Windows 10 upgrades are free for the support lifetime of the hardware; businesses above a certain size (the most likely ones to be conservative in their IT) have always paid for the latest version of Windows with their software assurance agreements, regardless if they deploy/upgrade to it.
Similarly alternative distributions are great, it's nice to have alternatives, but are also irrelevant to my point. Certainly in the Windows 7 support lifetime maybe you moved Ubuntu to Mint because you thought Unity was a mistake and maybe by now you are considering moving back to Ubuntu now that it is switching back to Gnome. The point is that you've still done many more distribution upgrades than Windows upgrades in the same timeframe and don't question it. (For the most part you'd still want the latest kernel and applications support, you mostly aren't just leaving machines be and not upgrading them.)
Not having more options in Windows upgrade direction is a fair complaint, but the point was that Microsoft in return granted one of the longest security support lifetimes of any desktop or mobile operating system out there.
I think it is useful to have that perspective on that, regardless of what you think about Windows or Microsoft. Whether or not Windows is moving the direction you want it to, the fact that so many people have the option to rest on their laurels for three more years before the next major scramble to a supported Windows version for their desktops (I'm ignoring servers and embedded appliances, this thread has always been about desktops), is largely unprecedented outside of Windows, and the refusal by some major corporations to keep Windows up-to-date would be laughed at if they were running Ubuntu or macOS.