Rose colored glasses. Remember Win 3.1's inscrutable "staple" icon? What the hell does a "yellow" traffic light mean in the context of Window controls?
And don't forget: software was shit when we were younger. Win 9x, Mac pre-OS X. Buggy crap all of it. I can't remember the last time my desktop hardlocked, though Android and iOS these days are similarly shitty to how Windiws 9x was.
Windows 3.1, for example. It had a very elegant Virtual Machine Manager with pre-emptive multitasking and true process isolation... and then GUI programs were all placed into a single cooperatively-multitasked event loop, because anything else would have killed performance. And the OS also had to continue to support IO device drivers written for DOS—that could disable interrupts system-wide and thus freeze the computer!—because otherwise your (horrible, un-QAed) scanner wouldn't work.
I fully believe that software hasn't gotten much better over the last 40 years. The hardware constraints have simply relaxed to the point that we're no longer forced to make as many Faustian bargains.
I guess we gain perspective. We have the stereotype of old people being cranky and stupid (like I come from the era of cd-rom cupholder jokes, faxing images of floppies, etc.), but probably there were intelligent old people out there telling us about missing context and we didn't listen or by its nature what they had to say couldn't get press or something.
I think you're on to something huge and important.
Some years ago I was working for an educational software company. We sold directly to schools. As expected, we'd get a lot of feedback from teachers using the product. For a while, everyone from the execs on down would ignore this feedback with a laugh. The majority of teachers we dealt with were absolutely clueless about anything involving software. Their reports reflected this ineptness.
One day, I had an epiphany that maybe, just maybe, these people were worth listening to. We went over the written feedback, translated their ramblings into something approximating proper bug reports, and it turned out they were doing a wonderful job of pointing out many of the problems (especially UI) hiding in our blind spots.
We had dismissed them because of a perceived cluelessness, and probably because of some internalized ageism & sexism (most of these teachers were middle aged+ women and most of my team was not). And yet when we finally listened to them, we put out an update which led to several accolades, a sudden drop-off in complaints, and probably our best selling product.
We were in a crunch to get version 2.0 out. Had the weekly progress meeting with the director. He had received some feedback from our remote sales team and he read one out loud that he thought was particularly funny. And it was, at least at first. Sounded like a old person flailing around with computers. But, then it hit me. This teacher was describing an edge case where a certain sequence of buttons would cause the whole program to lock up.
It was funny in part because the sequence wasn't something any of us would consider logical. So we had never tested for it. But I was able to duplicate the crash on my system and fixed it.
That was the epiphany. I convinced the director to push out the release date and we went through the backlog of ramblings and rants. Over half of them ended up being very useful.
CD-roms and disc media don't change for years, though. Popular apps change their interfaces every few months, it seems, and don't come with a manual. Learning the basics of a computer is more or less once-and-done, whereas keeping up with idiot designers is a constant task and a huge pain in the ass even when you're trying. And I say all this as a college student, which makes me one of the prime demographics for most of these apps.
And don't forget: software was shit when we were younger. Win 9x, Mac pre-OS X. Buggy crap all of it. I can't remember the last time my desktop hardlocked, though Android and iOS these days are similarly shitty to how Windiws 9x was.