I sometimes wonder what would've happened if the UI itself hadn't changed much; if Windows had retained those icons, that style, those ways of doing things. What if we had the Windows 95/98 look but with the benefit of 20+ years of polish and refinement?

Not saying I think their UI is perfect, but perhaps we'd see people feel a lot more familiar/comfortable with their computers, and perhaps it would also have inspired future generations not to constantly redesign things. Just as Apple became an inspiration for designers; it could have been the other side of that coin.

It's fun to think about.