Wow, I remember using
Unix back in the 1990s. I did some quite complex programming in
C Shell script on what were still known as
minicomputers in those days, this was at work and I remember being in my element. Firstly I had to learn how to use
VI which is one of the most non beginner friendly text editors ever, I remember using a keyboard overlay at first for all the key commands, people take user friendly text editors for granted these days, but with VI you can't even delete a character or move around the screen without remembering specific keys.
For people who are unfamiliar with the VI text editor, here's a video to give you a small taste of what a PITA it was for beginners:
Once you get used to it however VI does become surprisingly usable and it is capable of editing huge files on a basic terminal emulator, in fact it's still considered powerful even today. VI is still available in Linux, but mainly only old school users still use it because there's now a choice of numerous text editors that are much more user friendly with barely any learning curve.
I also remember
Windows 95 very well, plus I remember it's awful predecessor
Windows for Workgroups 3.11 which I was unfortunate enough to support in a networking environment at work for a good while, I say unfortunate because it was unreliable and temperamental to say the least, I constantly used to feel I was getting the blame for Microsoft's shortcomings when people complained about it's unreliability, expecting me to fix something that was impossible to make totally reliable at the time, but I had a damn good go. In those days Windows used to occasionally crash when it was heavily used, especially with networking, it was "normal" and you could only reduce it to a minimum, then I remember people attempting to share printers across the network, even with a patch I used to carry around with me on a 3.5" floppy disk it was very temperamental, especially printers that were shared via a PC rather than being directly connected to the network. Windows 95 was a welcome improvement even though it was still far from perfect, but I had to do loads of upgrades that became boring, repetitive and tedious, I remember also upgrading PCs to a minimum of 16MB of RAM because many only had 8MB which ran like a bag of nails on Windows 95, it's amazing how things have changed and we talk in GB now instead of MB (well it's now officially MiB and GiB, but I strongly disagree with this change that made established units GB,MB Etc. to the power of 10 instead of 2).
I think I understand why you want to use OpenBSD now even though you're severely restricted with what I would consider as obsolete graphics cards. Anyway I wish you the best of luck!