It was a genuinely great OS in its time.

OS/2 2.0 was released in the same month as Windows 3.1. In that era, it was so much better, it was embarrassing.

(Linux 1.0 would not be released for another 2 years yet, and v1.0 of native BSD on x86 -- BSD/OS from BSDi, i.e. still commercial -- for another whole year. Yes, it was possible to run pre-1.0 versions of both -- BSD/OS 0.3 came out in April 1992 as well -- but pre-1.0 Linux was very sketchy and very hard work.)

If IBM had let Microsoft make OS/2 1 a 386 OS (x86-32) instead of a 286 OS, the IT world would have turned out very differently. An OS/2 1.x in 1987 that could multitask DOS apps would have been a big hit.

I suspect Windows 3, FreeBSD etc. and Linux would never have happened. Perhaps the GNU Project would have adopted the BSD-Lite kernel, as it did evaluate but foolishly discarded.

But saying that, OS/2 2 was still a 1980s-style OS, a nightmare of vast config files, special drivers that cost money and came on floppy via international post, building custom modified boot floppies so your hard disk or CD drive controller would be recognised and real major pain.

The desktop was very powerful but very weird and kinda clunky. It's no coincidence that nobody has ever re-implemented the OS/2 Workplace Shell on Linux. Lots of other 1980s OSes -- Acorn's RISC OS; Classic MacOS; AmigaOS; NeXTstep; CDE; yep, all of those exist or existed. WPS? Yeah, no thanks.

PCs would not be able to boot from CDs in a standardised cross-OS way for years to come at this time. Indeed PCs didn't even have a standardised connector for attaching CD-ROMs yet. ATAPI would not be standardised for 6 more years. IDE was for hard disks and nothing else, and even EIDE had not yet appeared. CD-ROMs attached via SCSI (expensive, non-standardised) or on one of 3 or 4 different, nonstandard sound card interfaces (Sony, Mitsumi, Panasonic etc., all different and incompatible).

When NT 3.1 finally appeared, MS had a superb idea: copy the files from floppy or CD onto a DOS FAT partition -- FAT16 only, of course, FAT32 hadn't been invented yet -- and then run a DOS setup program. (This also worked fine for all versions of Win9x, incidentally.) DOS compatibility was relatively easy, thanks to the PC BIOS, which 32-bit OSes couldn't use. Anything would boot DOS off a floppy, and getting CD-ROM extensions or a simple network stack running was easy, especially if you didn't care how much RAM was left over. With a default configuration, you might not have enough memory left over to run any apps, but that didn't matter if all you needed was to copy some files.

So, boot DOS, partition the disk with a small C drive for DOS and the NT installation files. Copy the files on there, boot off the hard disk with no config files at all and run SETUP. It then created the big partition for NT, and in it, built a skeletal copy of the OS to install the rest. Then it installed a bootloader and rebooted the PC. You got a dual-boot menu, picked NT and continued.

This eliminated all the fooling around with making boot media with all the drivers you needed. It was much, much easier and quicker. I provisioned a whole network of client PCs this way once: no CD drives, just DOS and the Novell Netware client. They fetched the NT install files from the fileserver, and NT bootstrapped itself from there.

OS/2 never used this, which was very short-sighted of IBM -- I mean, OS/2 is more closely-related to MS-DOS than NT is. It's perfectly possible to compile DOS apps that can run natively on both MS-DOS, OS/2 1.x (16-bit) and OS/2 2.x (32-bit). They're called "family apps". The Setup program could have been a family app, but nooooooo.

You could install from HD to HD, but you had to boot into OS/2 to start the installation -- meaning that you had to edit the CONFIG.SYS file to tell it where to find the HD copy of the installation files. Could it automatically find them itself? Naw. Could you browse to it? Naw. What would you want to do that for?

I bought OS/2 2.1 as well, and most of my 2.0 drivers stopped working. I lost SVGA mode and I lost my sound card. At that point, I tried the beta of Windows "Chicago" (Windows 4.0, later renamed Windows 95) and it was amazing. It auto-detected my hardware, like magic. I got SVGA mode back, I got sound back, I got long filenames on FAT, and I even got a peer-to-peer network with my flatmate's machine over a Laplink parallel cable. (Networking was an extra-cost addition for OS/2, and later a more expensive special edition, "Warp Connect".)

OS/2 2's multitasking was great, but the OS wasn't all that stable. It was easy to have it running fine but you were locked out, because the input subsystem had crashed. (No networking, so no way to `ssh` in.) Large parts of OS/2 2 were still 16-bit code, too.

Win95's multitasking was as good, and while stability wasn't great, it was at least as good. It had vastly better compatibility with DOS and Windows 3.x drivers and apps.

I defected to the Microsoft camp and never returned. The bloated Win XP was the final straw and made me defect to Linux and Mac OS X on an old, cast-off, free PowerMac, thanks to XPostFacto.