I did a lot of development on OS/2 applications in the mid 90s, mostly on the Warp 3.0 version. Eventually we switched to Windows NT4 once it became clear that OS/2 had had its fifteen minutes.
I quite liked it at the time, but to be honest I think the wistful "could have changed the PC world completely" stuff I sometimes hear is just rose tinted nostalgia. It was a very good OS for its time; its main competition then was Windows 95, and there was certainly no contest there. But the NT kernel was a different matter, especially after it got a saner UI in NT4. There were no huge advantages to one or the other there (with one exception, see below). Compared to very different modern OSes such as OSX or Linux, OS/2 and NT4 were close siblings.
OS/2's one real Achilles heel, which gave us endless trouble, was the synchronous input queue, shared by all programs that had a GUI (including the OS desktop). The upshot of this was that, if a user-facing program crashed, it was very likely to freeze up the OS and require a hard reboot. When we switched to NT4, the vast improvement in reliable uptime was a breath of fresh air (if nothing to write home about by modern standards). I gather they partially fixed this in OS/2 4.0, but by then the writing was on the wall. OS/2 faded away before the rise of modern malware had really hit its stride, but I suspect the SIQ problem would also have led to all sorts of security issues. For example, look up "shatter attack"; that was bad enough on Windows, but I'm pretty sure OS/2 would have been even more vulnerable to that sort of technique.
While I certainly wouldn't claim that son-of-NT's victory over OS/2 had anything to do with its technical merits, I do think that, at least between those two lines of development, the (slightly) better OS won.