The first computers I ever used more than once or twice were the
Apple IIes - the first ever 'computer lab' at our school. We got them in 4th grade, and there were something like 9 or 12 for the whole school.
More, even, than
The Oregon Trail, I remember a program that we used to be rewarded with use of when we did really well (maybe in the gifted program?). The basic idea was a piece of paper with holes cut out and patterns or lines. Then, we were given a blank piece of paper and a hole-punch that only worked at a certain point onscreen and you could rotate or fold the piece of paper but you had to make it look like the one you were shown. I assure you, it was the height of 3D graphics with the being-able-to-rotate-the-paper part.
We got our first telephone answering machine sometime around 4th grade as well - and we were one of the first people I knew to have one.
Cable television was first installed in my neighborhood sometime around 4th grade as well.
We did not use
eight-tracks in our house - all albums (also known as
records or "LP") or
cassettes - but we had a car with an eight-track player and a few cartridges that came with the car.
In 5th or 6th grade, we got a
VHS instead of a
Betamax player.
I was working at my first full-time job when they hired a contractor to network the computers and install "the internet".
That was still during Windows 3.1, I think.
I was still at that job several years later when all of our industry software programs were rendered useless for a while due to incompatibility with Windows 95. The contractor couldn't come patch it up for a few days.
That contractor taught me a lot about what I know because he loved to talk while he worked and I was full of lots of questions.
It was before
Y2K and he told me that he was going into business for himself because he could make a lot of money for a few years because of that. And I believe he did.
What else? What's your age as measured by technological milestones?