Who is to say that an OS is "hipster rubbish". Whilst it is true in hindsight that OS/2 was only really a niche OS run only where IBM has significant sway over their customers, Microsoft did not have the same dominant position of either the OS or office application market that they do now.
I saw OS/2 deployed in anger as a desktop OS in IBM (of course), and in banks, utility and insurance companies, so it was used. And of course, it lingered in POS and ATM systems for many years after it left the desktop.
There were other OSs that were available at the time (both larger and smaller), and you have to admit that OS/2 was a capable OS. It just did not gain the market penetration that would have been required to merit it's onward development.
I would have been much happier if there had been more than one creditable and accepted OS in the years after OS/2 fell from favour, and before Linux was developed to a sufficient extent that it could be deployed on the desktop. It would have prevented Microsoft from dominating in the way that they have over the last 20 years. But history and the markets are fickle, as the developers of Betamax, HD-DVD, and many other technologies have found out.