The pattern here seems to be that the only way Microsoft can produce a Windows release that will be rated as "pretty decent" is by first subjecting their users to several years of a release that lowers the bar (or a subsequent release that makes an earlier one seem better in hindsight). 98 appears to have been the end of Microsoft's ability to ship consecutive major versions that were unambiguously an all-around improvement.

Windows 2000 was an all around improvement. The UI of win95/98 with the kernel from NT. Now 20 years later we see places for decent improvements. It's just that microsoft either didn't do them,or added more antifeatures than features.

Windows 2000 was definitely an all-around improvement over NT4, but it wasn't marketed as a successor to 98. That was Windows ME, which in hindsight was a bad idea. Microsoft should have abandoned the 9x line after 98 SE and put all their resources into making the NT line suitable as a replacement for the entire customer base. But for some reason they decided they couldn't pull that off in time for Windows 2000, and postponed the unification of the product lines until XP.

Great summary but I remember a few nuances.

Windows ME had some legit quality of life improvements over 98. Although 98se had a few of them already.

Winxp SP2 was good. OG winxp had its issues.

Windows 8.1 was pretty decent.

Windows 10 was a clusterfuck, from forced updates bricking machines to telemetry shoveled down everyone's throat to paid-for calculator to online accounts needed for local logins and all the way to its inbred UI. Total cluster, literally zero improvements to day-to-day use vs 8.1.

This. I didn't hate 8. I used it for several years without much trouble, and almost immediately regreted upgrading from it. I know a lot of people were put off by 8's UX changes, but they weren't that bad, especially compared to everything in your face AND under the hood that changed for the worst in 10. We even got the start menu back by 8.1 (and I never had an issue with the start screen, save issues navigating it with a mouse that were corrected IIRC).

Honestly, I even miss the charms bar/gesture; it was easy to make a larg general swipe and then choose "shutdown" to shutdown.

literally every point about windows 10 is wrong.

>forced updates

can be turned off with a few clicks, no external tool required, no command line anything. its just shy hard enough that people who should not do it wont accidentally figure out how. If you dont know how you know what to google for, if not you are one of thous people who should not turn updates off.

>telemetry

can be turned off mostly but not so easy. however its an essential part of how a modern OS is maintained people dont like it and I get why but fixing up bugs from just user bug reports is simply not feasible anymore.

>paid-for calculator

no clue what that means

>online accounts needed for local logins

simply not true. Ive used every windows from 95 to 11 and not one needes an online account. to this day I dont have one and beside the obviously cloud based apps like onedrive I can use everything just fine.

>literally zero improvements to day-to-day use vs 8.1.

pointless statement as it depend on use-case. plenty people only use office and a browser sure the OS updates have no use for them.

You're right, but equally you have to go out of your way to achieve that state. An everyday user with a fresh install will almost certainly end up with unrequested updates, telemetry and an online account for local login.

One thing missing in this discussion is DirectX. Windows 10 launched with a new version and tried to market itself as a gaming platform. People playing AAA games on PC is a sizeable market and this would've been a significant everyday upgrade for them.

Its intentional. If people could easily turn off updates they would do that and the next critical vulnerability would cause millions or billions of damage because it can infect and then use all those private PCs to attack other systems and no sys admin is around to fix stuff. It would be a disaster and very bad PR for MS.

I don't necessarily agree with this chronology, but even if it's true it seems fair for me to hate something that is forced on me just because it's new after I've just previously been forced to use something that's at best "pretty decent".

Add in 3.11 and take away 10 and you have my (now ended) history with Windows.