MS has excelled in getting price, (backwards) compatibility and system requirements correctly. That's why they moved slowly at the time and still do in some regards.
OS/2 was merged into Windows NT which is what almost everyone is using on desktop these day. IBM even tried giving OS/2 for free (Warp or 2.1, can't remember, you could get it by sending a coupon to the publisher), but the lack of compatibility and system requirements killed it. I remember booting it on a 486/33 + 8MB, yuck. Contrast that to almost instant startup of DOS and the requirements of an ordinary user.
Also, IBM sold PS/2 (or something like that) with OS/2 preinstalled... It booted like forever and there was zero software available for the home-user.