alt Hacker NewsI wasn't around in the 80's, since I hadn't even been conceived yet, so it's hard for me to really know what the landscape was like then.
Just reading about all the cool stuff that was available in the 80's, a part of me is kind of baffled that Microsoft was the one that ended up winning. DR-DOS and Concurrent DOS seem, at least in a lot of ways, objectively better than MS-DOS. I'm kind of surprised that Microsoft didn't just rip them off, honestly.
I 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.