I like being able to run games from early 2000s. Being able to write software that will still run longer after you're gone used to be a thing. But here we are with linux abandoning things like 'a.out'. Microsoft doesn't have the luxury to presume that it's users can recompile software, fork it, patch it,etc.. When your software doesn't work on the latest Windows, most people blame Microsoft not the software author.

Yeah, try explaining “drive C:” to a kid these days, and why it isn’t A: or B: …

Of course software developers are still stuck with 80 column conventions even though we have 16x9 4K displays now… Didn’t that come from punchcards ???

Windows can still run software from the 80's, backwards compatibility has always been a selling point for Windows, so I'd call that a win.