> But I do find myself curious how “lessons are learned” that lead to greater and greater tool exploitation in this brave new world.

(I think I'm reading this the right way but if not feel free to correct).

In a word: pain.

Until there's a legitimate threat to their well-being (emotional, psychological, or financial), the lessons won't be truly "learned." Until you know the true cost of a decision, you're flying high.

Older engineers have dealt with this organically so it's kind of encoded into their DNA. The very reason certain things aren't done (or a certain way) is because that pain has already been felt/encouraged learning a better way.