This isn't true at all. The ENTIRE industry had to re-invent itself MANY times - and MANY companies failed and have long since shutdown. Microsoft on the other hand has survived - and not only maintained backwards compatibility but embraced new technologies - and is doing so at a breakneck pace today.
Microsoft research is a top notch research company. Microsoft is also a large, if not the largest, contributor to Linux & Open source.
Horror stories aren't unique to Microsoft... The industry of the 80s/90s and early 2000s was something i'd never want to go back to - but its also something i suffered through and that suffering didn't matter what OS you ran. If you chose Irix it sucked paying 600 bucks for MEDIA to update your OS, if you ran HPUX it sucked having to buy a support contract to update your OS, if you ran Solaris, you were proud of solaris - but it wasn't until sun embraced open source that it really took off because we didn't have to buy a compiler that cost hundreds of dollars if not thousands to license.
Meanwhile, Windows has TurboC, TurboPascal and tons of stuff - and open source gnu started taking off and linux came around and the world started getting better for everyone- opportunity opened up - we crossed the chasim from 8 bit to 16 bit to 32 bit and 64bit and Windows has maintained a level of compatibility second to none to support all that legacy.
They're working hard to compete - Windows "S" mode is windows without the ability to stall win32 - its "Store mode" - it could go a LONG way into making it "suck less" from legacy cruft but by and large the market and developers are refusing to support it - which is odd considering they NEED to support the store model for official chromebooks, android apps or ios marketplaces.
Damned if you do, damned if you don't.