The dark side of rolling releases
One thing which I have always liked about Windows was that you'd get the big new version (WinXP, Win7) and any issues with it would be ironed out with service packs and patches. The result would be a better version of the original. The current version of Windows 7 which I am using on my systems is a better version of the Windows 7 which I originally started using in 2009.
I also don't have to worry about a next big upgrade breaking anything or changing anything fundamental about the way the OS works (UI or API level).
During the time that I used Windows 10 on a work laptop (Lenovo Thinkpad T470p), I found myself struggling with an OS that was somewhat like the Windows which I was used to, but also beset with issues (configuring IME input is either half-broken, or I have to RTFM) and the limited options for Windows Update meant that other than deferring updates I had to suffer through poorly timed automatic reboots.
A few rolling releases later, I had a Windows 10 that had gotten more features shovelled into it (admittedly WSL is slick), but which mostly still felt half-formed and incomplete. This also isn't going to get any better, as each year's update(s) has to be seen as a new OS release, according to Microsoft.
I'm not sure I could commit myself to more of this mayhem that comes with this, other than maybe opting for the Enterprise version (in so far as it's available...) and hopping from LTS to LTS version by the time its support lifespan runs out.
This basically makes it very easy to just stick with boring ol' Windows 7 until 2020 (and beyond?) instead and miss out on all the exciting fun that Windows 10 brings.
This makes me sad, because Windows has been my primary OS since 98 SE.