Windows closed maximized that don't open again maximized but in weird places (Outlook especially) or the "new trend" where they open with the same dimensions but are not actually in the maximized state (Docker Desktop).
The fact that you can't drag windows if their draggable parts are offscreen (particularly painful if the window bar is used for buttons etc and has only a tiny part where you can grab). Also ignoring Fitts's law, mostly concerning the close button.
The virtual desktop thing sometimes takes ages to load or crashes explorer.exe and often does not change the desktop when I tell it to (it goes back to the same one). Combine this with weird "flickering" that happens sometimes and it looks really fragile.
Once I had a two instances of PBI Desktop that were minimized but couldn't be unminimized again. Selecting them from the virtual desktop overview just made them appear briefly in the middle of the desktop with wrong dimensions only to fade away a split second later (fixed by going single-monitor and back).
Autostart applications that briefly flash a window and steal your focus (Bitwarden).
Task manager has this weird problem where in some situations trying to sort by a different column takes like 5 seconds and meanwhile the mouse cursor lags and stutters.
Oh, and rearranging my desktop icons when Windows feels like.
Overall things feel so slow and brittle at times it's maddening. There's more but can't be bothered now...