I like Windows 10. I've used every Windows version since 3.1, abandoning Windows 98, Windows ME, and Windows 8. That last versions I used very briefly, didn't like it, and quickly returned to the previous version. I thought Windows 7 was amazing, using less hardware resources for the first time ever, and I've enjoyed Windows 10 since I upgraded. In fact, I think at this point I've built 4 or 5 different Windows 10 machines from scratch.
I don't change hardware, but Windows 10 has evolved, essentially growing without changing versions. It had its 5th anniversary recently, and I was surprised to see a few articles like this one, that all talked about Windows 10 not being a success. News to me, since I've been happy with it.
It's interesting that the article talked about some of the promises of Windows 10 not being fulfilled. I don't know about the "free" aspect of it, though I do think Cortana was a bit of a failure. I didn't use it much, but I think the always listening and the issues with Siri/Alexa/etc. for speech platforms is an issue. I don't know many people that aren't geeks using Cortana, but perhaps this just isn't a useful thing in a non-phone OS? There are a few other things, but you'll need to read the article for yourself.
What I've noticed is that the evolution of the OS has faded a bit into the background. I do worry about updates, but I worry about lots of software updates. While quality has improved, the chance of being down is always disconcerting. While I haven't had any Windows 10 update issues across my 3 machines, or even any Android updates across the last 3 phones in 4-5 years, I still worry.
I also think the evolution of adding the Windows Subsystem for Linux is cool. I don't run a lot of native Linux stuff, but I do run Linux containers for SQL Server and I SSH into systems once in awhile, so I appreciate the native tools rather than some Windows port.
I do think we may get to the point where SQL Server versions fade a bit, with patches adding features, but I don't know we completely get away from versions. I think there's too much revenue from major upgrades, and since customers rarely want to make that investment, both for financial and time resources, means that I think we'll continue to get new major versions of SQL Server periodically, unlike Windows.
The one thing I'd like to see if SQL Server stop evolving the database structure, and allowing the restore of a SQL Server 2021 database on a SQL Server 2019 instance, assuming no new keywords are used. I don't know if we'll see that, but I know many people would like that.