Just as some off-the-top history, MS-DOS was clearly obsolete, but it hung around for like 10 years too long because people couldn't quit it. It was a DOSSY DOS world.
"Protected Mode DOS" went through the IBM/MS gristmill and became OS/2, which was a compromised product in a lot of ways. Then Windows (still mostly a DOS program) got a little traction, and Microsoft had hired Dave Cutler to write a real OS. And David overthrew Goliath and the rest is history. On topic, nobody really wanted protected-mode DOS or CP/M etc.
MS-DOS became obsolete only at the launch of Windows 95.
Until then, all the applications that could be found for Windows 3.0 or Windows 3.1 looked like worthless toys in comparison with the professional applications that were available for MS-DOS, despite the fact that the latter had to struggle with extended memory or expanded memory in order to use more than 640 kB of memory.
From 1990 to 1995, I had Windows 3.0, then 3.1, then 3.11 and I launched them from time to time, for fun, but to accomplish real work I always had to go back to MS-DOS.
Windows 3.0 becoming a hit was something unplanned by Microsoft originally - even the NT team was working with the assumption of using OS/2 API for applications. Win3.0 started out as skunkworks project initially hiding from management under smokescreen of just being one last release of "windows as application library" that some products (including 3rd party ones) were using