My first ever OS was a windows 95.
I remember my first experience with programming was windows 98 and purebasic. I made a trivia game.
The first computer I got close to was an IBM650 with revolving drum memory, punch card I/O and vacuum tube flip-flops. That was at the University of Western Ontario in 1961.
My own first computer in the 1980s was a Radio Shack MC-10 Micro Color Computer with 4KB RAM (upgraded to 20KB!), cassette tape I/O, Basic in ROM and a serial port. It connected to a TV set and had a 4 baud modem which required flipping a switch manually to connect. I used it to connect to my friend's account on the mainframe at York University.
I also made a game, but not trivia. I used peek and poke commands in the screen buffer to make the screen scroll in reverse and created an arcade-style action game called "Acid Rain". When I started dreaming in loops and branches, I packed it in and decided to come back to computers when they were more user-friendly.
That happened with Win95 and my first dial-up internet connection. Building rigs was fun back then... no plug and play. Lots of jumpers, specifying HDD parameters, etc.
Those were the days.
I imagine how much difficulty there was at that time, because it's not like today where there is Google/YouTube for any query (it really should be very difficult!)... In the past, people dedicated themselves to building and exploring really cool things, very different from today where there are infinite distractions....