Here's my own progression:
I used *I forget what* under MS-DOS to establish a PPP (SLIP? whatever) connection, ~1992, to a *nix host. It worked as well as MS-DOS could (and still does) allow.
Later, I used Telemate under MS-DOS to talk to the local Delphi dialup, to talk to Steve Jackson Games' Illuminati Online FreeBSD boxen.
Eventually, a local ISP showed up. I used Winsock on Windows, was disappointed: Things barely worked, which is saying a lot compared to all of the "barely worked" above.
I installed OS/2 on a 486SX with 4MB of RAM. The GUI loaded enough to see it, but then I discovered that OS/2 could run without a GUI: All command-line. It was fast. The TCP/IP stack robust enough to knock random other Internet users offline with a simple ping -f, all while my own connection was still useable: The pings would get longer and longer, and more and more infrequent, and then stop...even if I was on a different port of the exact same terminal server that they had been connected to, and even if asymmetric modem speeds said it shouldn't be that way.
Eventually, I got a Pentium 100 ("arguably overclocked" to a P120), and had 16MB of RAM on that board (16x1MB 30-pin SIMMS on carefully-stacked adapters). Worked a treat: I could finally use OS/2's GUI, and it was usable despite using 4x the RAM and about twice the CPU.
I used Linux after that, starting with Slackware 2.
I put on Windows 95 OSR2 after a then-employer handed me a copy of it and told me it was my job to do email support for his Windows-based software: I still did most of my work with a telnet/ssh session to SJ Games' io.com FreeBSD hosts.
As you can see, OS/2 was a blip on my own radar in those early days. But the Winsock days were really, really bad: Worse than the MS-DOS days.
And OS/2 was as solid as Linux, or the FreeBSD (then a mature thing) hosts that I paid by the month to use.
And OS/2's solid TCP/IP was included. With Windows, it was an extra, fickle (and not cheap, IIRC) third-party add-on.
95 OSR2 did OK, but meh. Nobody cared unless they were trying to get their new Packard Bell online, and then AOL by then the easiest answer. (They didn't get the money to buy Time Warner by accident.)