Why Windows 286?
Not Even Wrong: David Weise. It's all ancient history, but I have literally a thousand thoughts about what people thought was up with 386s and 286s and the comparisons with OS/2 :-)
The real issue is the "mode switch", which was nearly impossible on the 286. IBM had no 386 to shoot at when the idea for OS/2 was hatched, but they had ample time to change direction later, as "Windows 386" did. Once IBM got their plans right, they produced OS/2 2.0 and shortly after OS/2 2.11, which were fully preemptive OSes with a nearly perfect "DOS box", that is, a way of executing DOS programs in "virtual 386" mode. Windows NT was a solution to the very same problem, and a much inferior one until just recently. Windows 95 in contrast, and 98, 98SE, and ME, were still hybrids - cooperative tasking without full preemption. So Microsoft screwed the same pooch three times, and still won the game.
The "DOS box" on early versions of Windows NT was, in contrast to that of OS/2, a total disaster. However, it didn't bite many people because by then, Microsoft had also captured the market for applications.