Yes, the emulators have come a long way...! But still...it's an emulator...;)
Sometimes I wonder if it is better to just settle for a wine version. If it works, wine will always work, even in ten years. But I have a load of Lokigames that really need a lot of .so hacking just to get them to run.
OS/2...after warp I stripped OS/2 from my life and never looked back. It was my third version of OS/2. IBM did such a poor job with it--I had an on-the-shelf CD-ROM drive that ran great under Windows (which I was hoping to escape) but OS/2 did not support it! I asked IBM for a driver and their response was: just use the built-in Windows emulation! Grrrrr....;) That was it for me!
Well, Actually they are right: the supplier of the CD-ROM drive should have supplied an OS/2 driver. It's like that in the current graphics world too. Intel supplies linux drivers by making sure the opensource drivers work. Nvidia delivers binary drivers, and AMD delivers binary, and makes sure that the opensource drivers work.
At the time IBM had the money and OS/2 could have been a contender. But IBM just didn't want to match or exceed Microsoft's OS R&D budgets, and so OS/2 predictably failed. Can you imagine what a boon it would have been had IBM spent $500M (it was an $80B-a-year company then, richer than Microsoft or Intel) to get 500 of the leading Windows applications & games ported to OS/2? That and some serious hardware driver improvement would have put OS/2 out front. But as soon became clear, IBM simply didn't have any taste for competing with Microsoft on the OS front. Such a pity!
At that time IBM and Microsoft had a deal to develop OS/2 together. Microsoft had a habbit of stabbing partners in the back, so they went and developed NT, and made sure that IBM was not able to run Windows software by sueing them over the para virtualisation replacement IBM made to be able to run Windows in OS/2 protected mode. In the mean time Microsoft could just use everything IBM thought of for OS/2.
In the end I am glad OS/2 did not make it. Although it probably still is better than windows 8, if IBM would have had success with OS/2, they would not have invested time in linux.
Now there is just one common "enemy" with still a lot of anti-competition lawsuits, and one common linux in which about every company is investing.