Technology

Basically Microsoft tends to release operating systems in a 2 stage cycle. Every other version of Windows does something new and innovative, and then the next version is more polished, stable, and normal.

95 - new, innovative, and crappy
98 - solid
Then it got weird. They wanted to stop building the consumer version of Windows on top of DOS, and move it on to the NT kernel as 2000. The consumer version wasn't ready by the deadline, so they released 2000 for business only, and released a new DOS based Windows Me.
2000 - Really nice but boring. Extremely innovative new features for business use (Active Directory). The amount of work they put into Active Directory is probably why they didn't have the new consumer friendly UI ready in time. It's a rock solid OS but they significantly missed their goals.
Me - Absolute garbage, a cash grab. They basically put something out to satisfy the bean counters since they couldn't market NT to consumers yet.
XP - They finally pulled it off, and it's a pretty good OS that has the stability of NT, and all the multimedia features that consumers want.
Vista - They rewrote a huge portion of NT to be 64 bit, require signed drivers, and be more stable. The release version was pretty crappy but after 1-2 service packs it was actually pretty decent. But by then its reputation was already tarnished, and overall it was innovative and crappy.
7 - This was a very solid release. They took Vista and refined the UAC system to be less intrusive. Also a really nice new feature where you can use the taskbar like a dock where an app's icon stays in one place, even if it's not running.
8 - Experimental implementation of adding a touch UI to Windows. They made a decent effort but it really felt like a tech demo and nobody recommended it for anything outside of tablet devices. It was dreadful for people using traditional mouse and keyboard.
10 - Another solid OS. They basically took 7, added 8's touch UI features, and figured out how to blend them without it being annoying. The touch interface doesn't get in the way if you're using keyboard and mouse, and vice versa.
11 - I'm really not sure what the purpose of this OS is. I guess they're experimenting with trying to make the Windows UI more Mac-like. The taskbar centers the icons by default so it looks like the MacOS dock, and they're really pushing the new app store where all the apps have to be written with the newer UI libraries that work a lot more like mobile development platforms. So it really seems like Microsoft is planning for a future where Windows can run on many different types of devices and run the same apps. And Windows 11 is kind of a stepping stone to get there.
So Windows 12 should be interesting.

Also, while all of this is going on, with every new release generally comes a server version as well. They're constantly expanding the Active Directory schema and adding a lot of cool new features to Active Directory, such as new Group Policies that can be applied to groups of computers and users throughout an organization, which can automate a ton of things. If you want everybody in an accounting department to have a Q: drive with their QuickBooks files in it, you throw them all into an AD group or OU, and set up a new group policy on that group to map that Q: drive. And now all of those users will have that drive. I think it was starting with Windows server 2008r2 (Windows 7 server basically) and Windows 7, they added new Group Policies that did the drive mapping differently, and they would automatically map without the user even having to log off. Also, if the Group Policy is removed from a user, or a new user is moved into that group, it will automatically handle the changes. There's so much more to Windows than most people realize.