30 years in OS rollout for home and business use, I was also a beta tester for 9x.
Win 3.0 and earlier were awful. 3.1 was the first stable version and I used that for 10 years while using 3.11 for workgroups in a Lan Manager network.
Win95 was a step up but the first release was very crash prone. That said... Start menu. Windows has never been so easy to use.
This shows how easy - I have worked on French. German. Hebrew, Arabic and Japanese desktops. I installed and beta tested non-english builds where I didn’t know the language, before even seeing the English language version.
Win98 first edition was a mess, with a prototype driver model that broke certain classes of device. I beta tested 2nd edition after Microsoft sent me a free shrink wrapped version. Much better than FE but my TV tuner card never worked again (even after I reverse engineered the driver). ME was pointless, it just slowed everything down.
2000 was excellent and we replaced 9x on desktops. The corporate view was it was NT4 made stable, with plug and play. It needed every service pack though. Vista was like ME.
XP - good all round, especially if slipstreamed with extensive drivers. I had a universal OEM preactivated install disk for reinstalling home computers and I never found a machine it didn’t work on. Security on it sucked though.
Win7 - 2k with everything fixed and the good stuff in XP incorporated. Tiles replacing GINA opened up interesting use cases like webcam and fingerprint lock/unlock and multiple active logons.
Win8 - an abomination. Totally impossible to use as a development station, barely usable on laptops unless massively overspecced, no “I don’t have a touchscreen” default setting.
8.1 - only partially fixed the crippling of Win7 that went into 8.0.
10 - Since Creators Edition it’s been rock solid on every machine I’ve tried it. An old laptop that had been upgraded from 8.1 was dog slow until I migrated the drive to SSD and it now boots to logon in 11 seconds.
To use 10 properly without the telemetry you need Pro not Home, the latest feature version, minimum 8GB Ram and the OS on at least a SATA SSD.
If you have all of that there is LITERALLY no difference between it and Win7 in everyday usability terms - and, it’s faster than 7. And more secure. If the new interpretation of Start doesn’t float your boat, or you LITERALLY can’t cope with it having buttons as well as text, you can still party like it’s 1995 with a classic shell bodge.
The one thing I miss is F8 for safe mode.
So, worst: 8, 1, 2.
Bad but salvageable: Vista, 8.1, 98 first edition, NT4 until sp3
Average: 3.1, 3.11 for workgroups, 98 second edition, XP Media Center Edition
Best: 95 osr2, XP service pack 3, 7, 10.
Also, the crud you used to get preinstalled on OEM builds accounted for a lot of performance issues that you don’t get anymore.
The one OEM add that’s the exception is the laptop optimization for performance rigs. Power and graphics card management in systems with Intel and Nvidia graphics for example never worked as effectively on a vanilla Win7 install as it did with OEM Preactivated build; win10 on the same system is by far the best of the three.