I recall how a few years back I stumbled upon a classroom full of students with all new laptops all delivered with Win8.0 - Win7 still ruled everywhere and I had to admit I could not help them with anything on those boxes (to me they were as good as "bricked" even though they were supposed to be "functioning as designed.")
Meanwhile, the machines I work on still are on Win7, but a few of the others were installed with Win10 and they pretty muc do what they are supposed to (one is especially stable, but then it is never ever online and thus does not get any automatic updates
About a week ago I inherited a laptop with Win8.1 installed and you know what? I may not need to upgrade that to Win 10 as I first suspected - after having had a learning curve on 10 I can now work with this version of 8. Amazing!
Not sure if Win98SE or Win2000 was my favourite, but of all the versions that have come and gone since then I like the look and feel of Win7 the best - but I have to agree that lots of good progress was made in the underlying technologies (not including the spying and prying
And today, if I think of when you had to run in 640x480 mode at first until you had found the right graphics card driver, to name just one issue *network cards, sound cards, they all wouldn't work without you first finding and installing the correct drivers.) No, there has been some progress.
On the other hand, I have not forgiven MS yet for rendering a huge amount of old software (a good deal of which I wrote myself) useless by not supporting it on current versions of Windows. (Yes, I know of VMs, but hey, that's a schlepp in the end ...)