While it would be hard to call any kiloperson organization a hero, it is remarkable how people on the Windows team keep old software working even if it does not deserve to.
While the herculean task of billion-device compatibility has not always gone off without a hitch, the idea that the past was all gaffes and trial and error at Microsoft does not ring true if you read the above blog from one of its more prolific public writers.
Maintaining hardware compatibility with any PC hardware ever created is indeed nigh-impossible, so you'll note I didn't even mention that. I only talked about maintaining compatibility with applications written for their own operating system. Something that Microsoft does have pretty much universal control over.
The only mention I made about devices was regarding the printer driver issue with Vista, which had nothing to do with the devices and everything to do with Microsoft totally redoing their printer driver implementation on the OS level. It necessitated all drivers be redone and some manufacturers (like HP) took the not very admirable path of telling customers they were up a creek.
The most accessible documentation of this is Raymond Chen's blog. For example here's a piece written in 2007 about Windows 95 and DOS: https://blogs.msdn.microsoft.com/oldnewthing/20071224-00/?p=...
While the herculean task of billion-device compatibility has not always gone off without a hitch, the idea that the past was all gaffes and trial and error at Microsoft does not ring true if you read the above blog from one of its more prolific public writers.