This is completely wrong in a couple of ways.
Vista popularized 64-bit Windows, and 16-bit WoW (responsible for running 16 bit Windows programs) never made it to 64-bit Windows. This was true for the earlier Windows XP 64-bit, and it has been true for every 64-bit Windows that followed. So there's always been some confusion on this point, but note: 16-bit WoW exists even today on 32-bit versions of Windows 8. Today you have to enable it explicitly, but it is available.
Also, the NT-based versions of Windows never included DOS. They were never "with" DOS such that they'd need to "break with" DOS. The last Windows that included a version of DOS was Windows ME. The last Windows that included a version of DOS which anyone ever willingly used was Windows 98.
> Windows 10 is a full on multiplatform assault.
It's a pretty modest number of platforms compared to all those supported by NT in the late nineties. Although it will probably end up running on a lot more devices...
Tick.
Windows 7 was a refinement of Vista.
Tock.
Windows 8 was a new interface and a step toward multi platform, e.g. ARM.
Tick.
Windows 10 is a full on multiplatform assault.
Tock.
Running a big company is nontrivial. Microsoft's management has never been incompetent. The company has always been very profitable.