You might be right but still let me see if can get this analogy right:
The author is upset that we have to build a new house and we can't live in the old huts because they are not considered safe anymore.
The scrappy solution would be to to keep the hut as it is and build a wall around it. You still risk someone jumping over the fence though.
It’s more that you can’t live in a house now, you have to stay in a flat built and continuously maintained by others. Where before you could have built a simple, sturdy, and drafty castle that would stand for centuries, now you get a flat in a modern super-secure condo, which is very energy-efficient but requires constant maintenance not to crumble and decay.
> (At the same time this is necessary to keep HTTPS secure, and HTTPS itself is necessary for the usual reasons. But let's not pretend that nothing is being lost in this shift.)
So, to stay within your analogy: He acknowledges the need for new houses, but says that huts had a unique flair which is lost now.
I think in this analogy the issue I see it that we treat a one-man hut and airport terminal the same. For some buildings it's fine to have higher risks than others.
Of course people would need to be educated on those risks, which would probably be the biggest issue.