And when Windows 95 came out we didn’t exactly have 27” 4K monitors at our desks.

I still don’t really see the information density problem. You can fully customize the OS scaling way more than you ever could with older OS versions. Again, things like windows task bar icons and tray icons are the exact same size as Windows 7. Yeah they’re bigger than Windows 95 but I only had 800x600 to work with in those days.