Long time Windows user here, all the way back to Windows 2.0.
Windows 98 had some good things going for it, but it really was a crappy operating system. The interface was great, but It had a tendency to self destruct and could crash if you looked at it cross.
My all time favorite version is Windows XP. It was homogenous (one consistent control panel), compact, simple, and efficient. It was the first version of Windows with a good amount of reliability, rarely crashed and a lot of the problems with corruption over time such as "DLL hell" were resolved. The down side is it lacked native features, but there wasn't much you couldn't add with a third party program.
I think reliability is best it's ever been with Windows 10. In fact win10 is surprisingly robust.
The down side is everything else. It's a lot more complex, it lacks consistency (settings for some stuff, control panel for other stuff), it's a lot more cluttered, and it comes with all kinds of forced bloatware. In other words, software you can't remove and would never install given the option.
I can actually solve some of that bloatware problem with win10 by using the LTSC version, which I've been running for some time now. Still I would go back to Windows XP in a second if it was never deprecated. But then how can make MS and its partners make money without a forced upgrade path.
I've not heard much positive about win11 so I'll stay on win10 until I'm forced (as usual) to upgrade.
I've recently been messing around with XP on an old laptop of mine, it's a lot nicer than I remember it being and I'm honestly shocked at how fast it is on a single core laptop with only 512mb of RAM! Need to grab a stack of DVD-RWs sometime (for the first time in over a decade) to see how terribly Vista and ReactOS run on it - the bloody thing really doesn't wanna boot from USB unfortunately.
I actually thought XP looked like a toy OS full of bloat when it came out and way too flashy and trying too hard to be more 98/ME-like to attract consumers. 98/ME was pretty crap even if I have fond memories of gamimg on it, but it crashed all the f&@%£ time. You just learned to live with it. W2k/2003 was a whole lot more stable and a "real" OS, not some house of cards built on top of DOS. Boring, oh yes, and not many games worked at first, but stable and with networking that wasn't just an afterthought. XP was better for gaming and it was possible to de-LEGO-fy it somewhat. The silver theme was actually pretty ok, once you got used to it, but I don't miss it at all.
I didn't much care for W1.0, either. Or long pig, if you get that reference. 👴
Also: no blinking aero stuff and invisible borders !
I usually try to remove all that fluff as much as possible but windoze makes it harder and harder (who in their right minds want to hide ALL windows just because you jiggled one of them a tingest bit is beyond me...)
This might be a bit off topic, but Windows 98, and to a lesser extent Windows XP and 7, always evoke a sense of nostalgic simplicity for me. The OS felt stable (as in, unchanging) and seemed to stay out of the way.
Since Windows 8, but especially with Windows 10 and 11, it's felt complicated, busy, and intrusive.
I think the biggest problem is that, since 8, Windows has basically been trying to be two separate OSes, with two entirely different use paradigms, and it doesn't work. And having multiple control panels, configs, etc. makes things messy and confusing.
Totally agree on 8 and even 11 appears to be busy despite their intent for the contrary. That being said I feel like 10 will go down in history with XP and 7 as being simple and usable. I could have blinders on though because I've been using it for like a decade now.
10 was definitely the best version of Windows in a long time but personally I'd still put it closer to 8 and 11 than XP or 7, it's got far more advertising, telemetry, awkward inconsistency, and is more locked down/less customisable.
I'm a massive fan of skeuomorphic design, and Windows 98 was just so intuitive and practical. Things you could drag looked like you could move them, that bumpy texture thing was used in places it wasn't obvious already, and 3D made clickable things look like buttons.
I'm a software developer and power user, and Android surprised me by having a horizontally scrollable area with absolutely no indication other than the visible items didn't include something I was expecting to find.
I was barely alive in 1998, but I definitely think Win98 was the perfect sort of skeuomorphism, not super showy or maximalist like a lot of skeumorphic design is. It's like modern minimalism without the suck.