alt Hacker NewsI suspect it was largely IBM that was winning, for most of the 80s at least. MS was seen as being very much the junior partner.
Things started to wobble badly around 1988, with the release of the bug-ridden PC/MS DOS 4.x and the travails of OS/2 1.x. Most people doggedly stuck to DOS 3.3 despite its limitations (particularly the max HD size of 32 MB, at a time when 40 MB disks had become commonplace).
The IBM/MS wobble couldn't have come at a worse time for DR, though. Multiuser DOS was being discontinued, and DR-DOS wasn't mature enough until version 5 (the first to include ViewMAX) - by which time Windows 3.0 had already been released.
Honestly, Microsoft were very very lucky to end up in the position they found themselves in in the early 90s. The success of Win 3 was a shock even to them, and it utterly transformed the OS market.
Yeah, I guess I just like envisioning a universe where Gary Kildall was able to keep innovating and making cool stuff, instead of the tragic and depressing way that it actually ended.
I played with DR-DOS and OpenDOS in an emulator as well, and they both seem pretty cool, though bought of them were admittedly the later versions, and as I have stated a bunch of times, I really feel like Concurrent DOS and Multiuser DOS were way ahead of their time. Instead, the winner ended up being the objectively worse versions of things.