I have two hypotheses for why some kinds of software grow worse over time. They are not mutually exclusive and, in fact, may both be at work in some cases.

Software has transitioned from merely complex to chaotic. That is, there is so much going on within a piece of software and its interactions with other pieces of software, including the operating system itself, that the mathematics of chaos are often more applicable than logic. In a chaotic system, everything from seemingly trivial differences between two ostensibly identical chips to the order in which software is installed, updated, and executed has an effect on the operating environment, producing unpredictable outcomes. I started thinking about the systems I was using with this in mind sometime in the early 2000s.

The "masters" in the field are not paying enough attention to the "apprentices" and "journeymen. Put another way, there are too many programmers like me left unsupervised. I couldn't have had a successful career without tools like Visual Basic and Access, the masterful documentation and tutorials they came with, and the wisdom to make sure I was never in a position where my software might have more than a dozen users at a time at any one site. Now we have people who don't know enough to use one selection to limit the options for the next selection juggling different software and frameworks trying to work in teams to do the bidding of someone who can barely type. And the end result is supposed to be used by thousands of people on all manner of equipment and network connections.

One reason that open source software seems more reliable is that people like me, even if we think we can contribute, are mostly dissuaded by the very complexity of the process. The few of us who do navigate the system to make a contribution have our offerings carefully scrutinized before acceptance.

Another reason that open source software seems more reliable is that most of it is aimed at those with expertise or desiring expertise. At least in my experience, that cohort is much more tolerant of those things that more casual users find frustrating.