XP was fine. 2000 was good. Nobody pines for Windows ME. People said those things and they meant it. Windows 8-11 feel pretty bad, overall. 7 was okay.
XP was fine because you could throw it into 2000 mode, though looking back the fisher-price UI was just the UI.
Windows Vista wasn't terrible if you had a beefy machine and well-supported hardware. 7 was basically Vista but with newer machines and better hardware support. 8+ has been meh.
Adding a search to the start menu is huge and completely changed how I use it -- I almost never do anything besides hit the Windows key and start typing a search query. Besides that, the way nested menus worked was frustrating and I'd frequently waste time doing things I didn't intend trying to navigate them.
That explains it. I use win+R (the hotkey for run) the same way since I think win95.
When I search the start menu, it does the weirdest things, e.g searching notepad via bing instead of starting it, or preferring the uninstaller above the real program. So I learned that the start menu is basically broken for search, and became harder to use as a menu. I mostly abandoned it.
Meanwhile, the gui widgets, built in windows and control panels became much worse and dumbed down. It pretends to be a helpfull assistant, but behaves more like an arrogant drunk. I want to do some work on the machine, not be told about some experience it really wants to shove in my face.
Well, the difference is Windows + R I would need an exact command and the search bar I don't. I share some of your frustrations about the relevance of the top result but still, partial matches are important to me.
What they have today is an UI disaster: cannot tell which window is active, scrollbars are so 90s - nobody cares about them, settings would make Google proud - one cannot know if the text is only a description or it starts a config dialog, 1 px window border - good luck resizing on a 4k monitor, gray on gray, titlebar highjacking, hard drive hidden in explorer beside virtual folders etc.
