Oh, it's fine. At your leisure. I didn't mean to go against the assertions themselves, but more just kind of speak to their "unargued" quality and often sketchy presentation. Even that Simon piece has a lot of this in there, where it's sort of "by defenition of 'complexity'/by unelaborated observation".
In engineered systems, there is just a disconnect between on our own/small scale KISS and what happens in large organizations, and then what happens over time. This is the real root cause/why, but I'm not sure it's fixable. Maybe partly addressable, tho'.
One thing that might give you a moment of worry is both in that Simon and far, far more broadly all over academia both long before and ever since, biological systems like our bodies are an archetypal example of "complex". Besides medical failures, life mostly has this one main trick -- make many copies and if they don't all fail before they, too, can copy then a stable-ish pattern emerges.
Stable populations + "litter size/replication factor" largely imply average failure rates. For most species it is horrific. On the David Attenborough specials they'll play the sad music and tell you X% of these offspring never make it to mating age. The alternative is not the https://en.wikipedia.org/wiki/Gray_goo apocalypse, but the "whatever-that-species-is-biopocalypse". Sorry - it's late and my joke circuits are maybe fritzing. So, both big 'L' and little 'l' life, too, "is on the edge", just structurally.
https://en.wikipedia.org/wiki/Self-organized_criticality (with sand piles and whatnot) used to be a kind of statistical physics hope for a theory of everything of these kinds of phenomena, but it just doesn't get deployed. Things will seem "shallowly critical" but not so upon deeper inspection. So, maybe it's not not a useful enough approximation.
Anyway, good luck with your housing meetup!