I worked for a company with a wild mix of DOS, Win 3.1, and Win 3.11. Then we got new PCs, some ethernet hubs and switches (instead of the damn coax cable with terminators) and started to move to Win95.
Win 95 was a beast. It came in a bunch of floppies. It took ages to install, and you’d find after one hour that the last floppy was corrupt. Also, on our cheap hardware (Siemens-Nixdorf Pentium PCs) sometimes the sound card or the ethernet card would go missing. Nothing short of a reinstall would solve it. Temporarily, of course.
The Win 98 came along. All our problems were solved. It was a 32 floppy install job, if memory serves. No, no CDs on our company. Still, it crashed a lot, and Microsoft Office had a tendency to simply destroy 100+ page documents when it was not crashing.
At home I used Windows, because how else am I going to play games, right? But I kept experimenting with Linux, and liked what I saw. There were many pieces missing (no USB for a very loooong time, for instance), but what was there was rock solid compared to Windows. And you could COMPILE YOUR OWN DAMN KERNEL, fer chrissake! How powerful was that?
Eventually, distros started to emerge that made some pain points go away. I remember Corel Linux, Caldera Linux, Mandrake, RedHat, etc. I settled with Debian because ‘apt-get dis-upgrade’, of course. Then Ubuntu came along and made Linux more pretty and usable for simple folk. They even sent you a free CD by mail if you asked them.
I got ever more tired of Windows nuking my boot sector, the viruses (virii?), the hunting around for drivers, the having to throw away good peripherals because windows thought were too old to support.
I made a choice and dropped Windows. I missed a lot of the gaming scene until Wine and Steam caught up with the state of the art. In the mean time I made use of emulators and had a good time playing console and arcade games.
Oh I was teased about it. Fellow IT workers (proper MSCE type people) would give me a hard time because “Linux has no future”, “Unix is dying”. I guess the future proved I was right. I now earn more that they do.