It truly depends on the quality of the software you were using at the time. Maybe the software you used didn't result in many issues. I know a lot of the games I played as a kid on my family's or friend's Win95 machines resulted in system lockups or blue screens practically every time we used them.

As I mess around with these old machines for fun in my free time, I encounter these kinds of crashes pretty dang often. Its hard to tell if its just the old hardware is broken in odd ways or not so I can't fully say its the old software, but things are definitely pretty unreliable on old desktop Windows running old desktop Windows apps.