This is because since at least ‘95, MS has alternated focus between base technology and polish/reliability/UX. The ones we think of as good (98SE, 2000/XP, 7) are the ones with the focus on polish. The ones we remember as flaky (ME, Vista, 8) are the ones with substantial new tech in them that hadn’t had the additional years of refinement.

I think Windows Me was just an attempt at making 98 more modern and multimedia-friendly. It was just bad, with no relevant upgrades at any layer of the stack.

i think it was the only still dos-based windows to automaticall install usb drivers for mice and usb sticks and things. we had a sony laptop running ME for a long time because it was too slow to run XP, but had a USB port already

Yeah, actually let’s not talk about Windows ME. :P

What was the new tech in ME ?

Yet, NT4 -> W2K -> XP.... strange how the consumer degraded but the business was a real progression. I was using NT4 at my first job in 98, through till 2000 became more wide spread. Win2000 was a step up, but the driver support (IIRC) could be a bit spotty. But overall it was great. Then XP came a long and added Crayola UI and Zip folder access. It took me a lot longer to move to XP, and when I did I would always go to Control Panel and turn off the dreadful UI and make it go back to using the classic desktop style. But XP stayed relevant right up till 2013 when I changed jobs and no longer needed to use VMs as much... even then there was still one VM I needed to use that was supplied by head office. So XP for me was still in use when they EOL'd it, though only to run a legacy simulation in a VM.

W2k was the first possibly-not-utter-crap version. In the consumer space W3.1 was just DOS with Windows, and didn't even have full multitasking.

W95 was 60% bugs and 40% OS. There was even a really obvious bug in the calculator app. There were all kinds of very very weird - i.e. bad - design decisions both in the code and in the UI. Trying to find fixes and workarounds literally wasted days of almost everyone's time.

The initial release of XP was workable, but by SP1 it was fairly stable and you could actually use it as a working OS without having to deal with driver issues and constant crashes.

Vista was another dog. W7 was very possibly the best Windows. 8 was another WTAF release. 10 is 8 with some improvements, but some added evil in the form of forced telemetry for most users, and such.

For me, Windows 95 OSR2 (OEM service release 2) and 98 were more stable than stock 95. I remember having to obtain it via one of those "100 in 1" pirated CDs, because the OSRs weren't made available to the end users.