"Installing OS/2 wasn’t very hard, but you couldn’t guarantee it would work on your hardware, and at about a thousand bucks a go this was an expensive experiment."
Sorry, but that's not entirely true. There were plenty of lists supplied which provided in every detail which hardware components were and which weren't supported. It was relatively easy to look this up before you started. Even the IBM OS/2 website was very easy to use when it came to finding these lists (which was pretty much amazing considering how a lot of other information was burried between huge amounts of totally confusing links and pages).
Still; if your hardware (-components) was (/were) mentioned as being supported then 9 out of 10 cases it would easily work. The only time I had major issues with OS/2 was when I actually bought myself an IBM (iirc an Aptiva) with the sole purpose of running OS/2 on it. I mean; if I got myself a /real/ IBM computer, surely it should do wonders with OS/2? Guess again!
Which was partly my own dumb fault; I assumed IBM cared. Which IMVHO is what really killed OS/2; IBM themselves. They didn't seem to care one bit. Take the Aptiva; did it come with OS/2 drivers? No; only Win95. The 486 Compaq I once had supplied drivers for just about anything; /including/ OS/2 (not directly but on demand; I recall purchasing a huge amount of drivers and support software; 3 boxes of 3.5" disks which also included plenty of OS/2 drivers).
I even contacted IBM support with this (considering how I was entitled to support through purchase of my new PC). Needless to say, but they didn't quite manage to get beyond "We think it should work...".
But its the weirdest thing; on the other hand IBM did quite a bit of good. I for once was very impressed how Sun's Java (back then a rather new environment) had found a rock solid home within OS/2. Not sure about OS/2 3 ('Warp') but Merlin (the one with the nice pull down menu) supplied Java right out of the box. That was impressive for those days, at least IMO.
There IBM did manage to do the right thing; Java support really managed to extend the stuff one could do with OS/2; now you weren't merely "limited" to your common DOS batch, OS/2 cmd or Rexx scripts. (not that you were really limited; man... I still vaguely recall the stuff one could do in a cmd file. Sjeesj!).
No, if only IBM would have cared a bit more; imagine OS/2 under the supervision of IBM as an open source project, but not in a way where it would only cost IBM money (like Sun did), but in a productive fashion... That could have easily become a power player which could have gone toe to toe with Windows today.
IMVHO of course.