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It was always bad.
Windows 3.1 was bad. It was ugly, it was slow. The Macs of that era looked better, although their multitasking was even worse than Windows, somehow. It was pretty clear that 3.1 was just a desktop GUI over a text OS.
Windows 95 and 98 were bad. They were graphical improvements over 3.1 / NT, but they were so brittle and janky. Remember bullshit like "TEXTFI~1.TXT"?
The latest versions are all terrible too. Like, try to make a change to a system setting and you get the Windows 10/11 themed settings menu. But, if you try to make any kind of advanced setting change and you're taken over to a GUI that shows that under the hood it's still effectively running Windows XP components.
I thought Win 2000 was an improvement. Didn't Win 3.1 literally run on top of DOS? Like, DOS was the actual operating system and Win 3.1 was merely the graphical user interface/desktop environment, so it consumed a bunch more hardware resources? I think I remember having to run many programs out of DOS so that they would run more smoothly than if I used Win 3.1. In that sense, Win 3.1 was really Ski Free, Space Cadet Pinball, Solitaire, Minesweeper, and a nice file manager.
I also liked the improvements of Win Vista, but my laptop couldn't seem to keep up with the requirements needed for things to run smoothly. Win 7 seemed like a smoother Win Vista, so that was nice. However, I felt let down that there were no major noticeable improvements other than performance, which could also have been attributed to improvements in hardware. Around then, I started experimenting with Linux out of sheer curiosity and slowly switched to Linux 100%. In the past several years, I know about Win only from what I hear on Lemmy, so ofc I think it's terrible, but I wouldn't know from personal experience and judgment. I'm happy af with Linux anyway.
Windows 95, 98 and ME were all DOS based.