On the philosophical side, one thing to consider is that NT is in effect a third system and therefore avoided some of the proverbial second system syndrome.. Cutler had been instrumental in building at least two prior operating systems (including the anti-UNIX.. VMS) and Microsoft was keen to divorce itself from OS/2.
With the benefit of hindsight and to clear some misconceptions, OS/2 was actually a nice system but was somewhat doomed both technically and organizationally. Technically, it solved the wrong problem.. it occupies a basically unwanted niche above DOS and below multiuser systems like UNIX and NT.. the same niche that BeOS and classic Mac OS occupied. Organizationally/politically, for a short period it /was/ a "better DOS than DOS and better Windows than Windows" with VM86 and Win API support, but as soon as Microsoft reclaimed their clown car of APIs and apps it would forever be playing second fiddle and IBM management never acknowledged this reality. And that compatibility problem was still a hard one for Microsoft to deal with, remember that NT was not ubiquitous until Windows XP despite being a massive improvement.