>perhaps the most critical aspect is that the perverse incentives are left to the judgement of users with little to no understanding of the system or the wider implications of misusing it.

This is true of capitalism and democracy. The worst choice for economics or governance except for all the other choices. I want a system that respects the users judgement not yours. No matter how well meaning you can't adopt the perspective of all users nor do I desire to see the mediocre results of smart people who know better than their users trying.

It's actually not that hard. If you make updates something that silently happens periodically without interrupting the users or making many changes to the UI that the users rely on they will let you update the parts they don't directly touch all you want to secure their systems.

When you want to make major changes make them opt in and test them to ensure they are actually substantially superior. After a while deprecate the old UI. People will tolerate infrequent major changes far better than constant small breaking changes to their workflow.

Again if you don't make updates suck you don't have to coerce people into doing them. If you are figuring out how to coerce users for their own good you are solving the wrong problem.