This is my list of windows versions that I rank by my opinion of their usability and abilities "of their time". That is, not ranked by comparing them to current standards, but comparing them purely by how they operated in their hayday. This is purely my opinion, and you will most likely disagree with it.
Personally I don't have much respect for Windows, but it did have a few highlights during its time. So here goes. I award the number one spot to:
1. Windows 7
Yes, Windows 7 is, in my opinion, the pinnacle of excellence for Windows. Everything before this has been building up to it. Everything since has been a gradual dumbing down and crippling of the system.
2. Windows XP
The venerable operating system that many people are even now still using. Things have moved on since then though and much software won't work on it, but it's still a decent effort by Microsoft. Some may argue that XP is better than 7, but I disagree. 7 keeps what is good with XP and adds to it with new facilities and APIs making things work better and easier.
3. Windows 98
This is when Windows started actually looking like it might get good. Yes, it's still in its infancy, but it's out of short trousers now and beginning to be a respectable system.
4. Windows 10
This one could have been as good as Windows 7, and in fact
it started out looking like it might be 7 with additional facilities.
However that was not to be. The direction Microsoft have taken with this
version, of gradually removing facilities and hiding things
behind bigger buttons with fewer options, means that getting things done
here are harder and more frustrating than in 7.
5. Windows 2000
I used this for quite some time in parallel to XP. It's like XP but more business oriented. Not so good for games, but better for office work. It's basically the beginning of the attempt to merge the Windows NT and Windows 95/98 branches into one. It worked well, but didn't quite have the appeal of XP.
6. Windows For Workgroups 3.11
This was a classic. It really was the peak of the pre-95 versions of
Windows. With the "advanced" networking facilities (advanced by the
standards of the time) it started bringing simple networking to the
7. Windows 95
A groundbreaking operating system. And as with all groundbreaking operating systems it broke, and ground to a halt. Well, maybe not, but it wasn't as good as Windows 3.11 was when it first came out, and was soon replaced with Windows 98.
8. Windows 8.1
This really was an attempt by Microsoft to save face. They messed up and they knew it. And not for the first time. Windows 8.1 was an undoing of the mess that was Windows 8. And because of that it was barely usable. More usable than Windows 8, but still a horrible mess. Still, there are worse things.
9. Windows Vista
An attempt to revamp XP with a funky new interface. And in the process making one of the least stable operating systems ever. They really messed up the internals with this one. Cough at your computer in the wrong way and it crashes. Plug something in and it crashes.
10. Windows 8
This one was just spiteful. A bunch of Microsoft managers gathered
together in a conference room and asked "What is the single most used
facility in Windows?", the answer to which is "The start menu". And the
decision they came to? "Delete it."
11. Windows ME
Does anyone remember Windows ME? Did anyone actually use ME? If you thought Windows 8 was the worst ever, then obviously you never experienced ME. I did. It really was the all-time depth of vileness. If you were to take Vista and cripple it like Windows 8 you might end up with something like a modern version of ME. The least stable, least usable version of Windows ever. Ghastly. There's even an XKCD cartoon that plays on how bad it is:
You may notice a trend to this. A pattern. And there is one. Microsoft have very much taken a "Change. Fix. Change. Fix..." attitude to development, as can be seen in this table:
They introduce a new design. A new interface, new ways of doing things, etc. And that is not good. Too much changes too soon and things break in nasty ways. Then the next version they fix those things and you get a better version.
As you can see, though, it broke down after 8. 8.1 was the "fix" to 8, and they skipped 9. Why skip 9? Some people say "because 7 ate 9". I say it's because 8 (and 8.1) were so bad there was no way to fix it in a new version, so Microsoft just cut their losses and aborted it, focusing their efforts on Windows 10 instead. Windows 10 is what Windows 8 was intended to be, but learning from that horrible mistake.
Windows 10, of course, breaks all that now. No more new innovative designs. No more cleanups and improvements of that innovation to give us good (or at least reasonable) versions of Windows. Just a steady trickle of degradation of the system until it's eroded away to a homogeneous lump of crud. Windows 10 is the beginning of the end for Windows. It's like they're steadily winding down that part of their development resources. Just a steady reduction of everything: quality (just look at the October 2018 release fiasco), usability (things are being dumbed down till they get back to Windows 8...), even the looks are fading.
In some ways its a shame. Windows did a lot to bring computing to the masses (is that a good thing? That's another rabbit hole...), but it is certainly waning now. But in other ways it's far from a shame and some rejoice in the fact that Windows is not the powerhouse it once was. There are so many other options available now that Windows doesn't make much sense any more. But it's still seen as (and aggressively pushed as) the default operating system on any new computer. Even now in 2019 it's almost impossible to buy a new PC without Windows on it. Yes, there are a few specialist sellers, and a few of the mainstream sellers (such as Dell) do offer a few models with Linux pre-installed, but everything else is "You must have Windows whether you want it or not. No, we won't sell you one at a discount without Windows. You have Windows or you don't buy it."
"So buy a Mac" you may say. Uhhhhhhh..... don't even get me started on Apples..... Overpriced piles of junk that are only surviving on the remnants of past glory. I used to use a Mac. I had a dual processor G5 Power Mac (one of the big metal beasts) with Tiger on it. That was an amazing computer and an amazing operating system. Since then they have switched to Intel (now they are little more than a shrunk down PC), the build quality sucks worse than an ESCOM PC (do you remember ESCOM?) and the OS now is only really usable by people who are more at home finger-painting.
So for me it's Linux every time unless I have a specific requirement for Windows or OS X. And that is getting rarer and rarer now. And it should be Linux for you too. Don't be scared of Linux. It's not the monster it used to be.