I tried to give OS/2 a try, but what happened was kind of bizarre. I had a DEC PClone with a 486 (cannot remember if it was DX or SX) inside. OS/2 needed a graphic driver for the S3 chip. I called DEC support to ask for the driver and they said they didn't have it but IBM did. The DEC rep kept me on the phone while he called the OS/2 support number. DEC had incredible service at the time.
Then the bizarre happened. The IBM support person said I needed to sign an NDA to get the driver. Both the DEC rep and I tried to explain to him I was a humble end user and not interested in anything but the driver. There must be a mistake as I did not want source code. Nope, just the driver required a NDA and some verification. I said I would think about it, and we hung up. The DEC rep apparently had quite a few people gathered around him and they were laughing pretty hard. He then asked if I would like a nice copy of Win NT with no NDA and all the drivers for my machine.
I used to do OS/2 support as an IBM co-op back when I was in college. In many ways it was pretty sweet -- I did some cool stuff with the built in Rexx interpreter, which -- though not as or widely supported as, say, perl -- was still pretty nice.
Regarding your specific problem, I'd add that IBM's support structure was byzantine, with multiple groups with different agendas and tons of snafus like: "this isn't our issue, contact Thinkpad support," followed by "this isn't a Thinkpad issue, contact OS/2 support." (Aside: I once tried to get a different IBM group to handle an issue I believed to be theirs, and after getting rebuffed multiple times, I wrote a rather angry response which got me in trouble with my manager. Learned a lot from that -- mostly, don't write angry.)
9 times out of ten, the issues we received boiled down to a) missing / out of date drivers for some piece of hardware (as in the S3 chipset you mention), or b) incompatibilities/errors running existing windows apps. I think OS/2 failed for a variety of reasons, but ultimately, even though it was better than windows (for a while), people just didn't feel a strong need for pre-emptive multi-tasking, so it was never a strong selling point, especially if it meant you couldn't run the latest PC games.
Then the bizarre happened. The IBM support person said I needed to sign an NDA to get the driver. Both the DEC rep and I tried to explain to him I was a humble end user and not interested in anything but the driver. There must be a mistake as I did not want source code. Nope, just the driver required a NDA and some verification. I said I would think about it, and we hung up. The DEC rep apparently had quite a few people gathered around him and they were laughing pretty hard. He then asked if I would like a nice copy of Win NT with no NDA and all the drivers for my machine.
I really wanted to like OS/2.