I can't remember where I read it, but I read something along the lines of: "Technical debt is just code nobody can read anymore." A lot of us old timers have seen so many paradigm changes that we just don't care - we are focused on whether it solves the problem and whether it is maintainable.
Switching from the "hot" framework we started using last year to the "hot" framework that everybody loves this year is a step backwards from actually solving any problems. And two steps back from being able to maintain the resulting system. The world of startups is so very "now" focused that I think a lot of people (especially on Hacker News) forget that most programmers are still dealing with code written 20, 30, 40 and in extreme cases 50 years ago.
Better is great. Easier is great. But most old code can't be refactored, only replaced. Which means everything that interoperates with that old code has to either be replaced or it has to work exactly the same way. Sometimes that makes sense. Sometimes that's an absolute disaster.
Something that looks "simple" to you really can be too complex in a greater context. Rant all you want, this is just a fact of life. The software development profession has been so fascinated with shiny new toys for the past 25 years that we tend to forget that the hidden (and dangerous) part of the iceberg is not only in the past, but what we're creating now will just make it all that much bigger and more dangerous unless we're very careful.
But. I know places that are so stuck in the past that they are paralyzed and can't do anything at all. There certainly is plenty of "we've always done it this way" that needs to be thrown out the window. Introducing some new workflows or tools could really simplify things moving forward. The problem is knowing which is which. In order to know which is which you need someone who understands the system(s) at a "heroic" level.
I see us moving that way with things like "full stack" or "devops", but those are mostly only considering newer software. Making 30+ years of IT infrastructure work effectively and efficiently really is an epic task. And not one most CIOs I know of are at all capable of.
Sorry, I guess you triggered a flood of things I've been thinking about this past year. I guess I would sum it up by saying that your own rant is very personal and doesn't necessarily take the context that software is developed within into account.