1. Sure everything is hard. My point was cryptography is hard in the same way as building a 5 story stone building is hard, while surveilence avoidance is "solve human beings" kind of philosophical problem.
2. The question was mostly to demonstrate that you would have a hard time coming up with such an example, because free software/hardware was never adopted in any significant way, so your argument that it was and it didn't work is not true. Free software being abused by existing/new monopolies to further their goals is not free software facilitating it. What happened would have happened regardless, and what little freedom and privacy we have today in software is thanks to free software. If free software ideals were truly adopted and not circumvented in every way possible the problem might have been more or less solved by now. I don't see how this comes in conflict with any governance system. Not being able to blindly follow the exacty same practices as before in a completely new industry is not exactly an unexpected and unresolvable conflict. Why can't a surveilence (capitalist/state/other???) system run on free software/hardware? My whole point was it can and it should, and if everyone does the absolutely embarrassing situations like the one in the OP can be avoided.
3. Well we might be arguing different things, but from my point of view it's you, who is bringing in philosophy and politics into purely technical and much more severe issue. In the context of the issue OP presented there were no vague _emerging properties_ or _capabilities_ or anything else as complex as you are trying to imply. It was a simple failure of a very real and tangible system, it's literally the locks to your house being master keyed without your knowledge, not because it was hard to figure out, but because you were not allowed to look inside or have a local locksmith look inside and that was(still is) considered normal. And because it is considered normal there actually are no local locksmiths who would evaluate even "free and open" locks, because it's not a profession one could make a living off in a world where people are not allowed to look inside most locks.
4. It was not an ad hominem, it was an exaggerated analogy. I threw in the caveman for some extra spice not a central point of the argument. A modern 5 story building is much more complex than a tent or a cave. It is BOTH much more capable and much more reliable, even if you include human factors... not philosophy though, I guess a philosopher would argue that a building is a "simplification" of a mountain with caves, and a tent is way more "complex"(or "reliable" take your pick of nosense) than either of those.