The corollary is any system where users can leave without pain is a system that has low investment appeal.

If you talk to investors they will say things like "we need a moat." A moat is exactly the opposite of what the author wants in the systems they want to use. Those who have money to invest generally aren't those who have higher ideals than money.

Competitors will seek to destroy things that challenge their power. One could imagine paying for large amounts of bad faith content in order to destroy a system's value by incurring moderation costs. So now you have a system that is not only unappealing to invest in, but must also defend itself from the resource expenditures of competitors attacking it by spending resources on defense.

> If they understand that forcing you to enshittify the service will send all your users packing and leave them with nothing, they will very likely not force you to wreck your service.

They would have never invested in the first place, making this statement self-contradictory under conditions of philosophical rigor. There is no way under Doctorow's philosophy to build an institution that could challenge a stronger institution. There is a clear bootstrapping problem to his ideology.

All collective action problems involve the exercise of responsibility, doing what must be done even if it harms you or isn't short term optimal. The author is trying to exercise responsibility by holding an ideological line, but doesn't do much to challenge power other than to assert the illegitimacy of power itself as an absolutely corrupting force.

But institutional investment is what builds entities strong enough to challenge other entities power.

The ultimate failure is the irresponsibility of getting something for nothing, because the cost of that "nothing" is submission.