Also on a more optimistic node: when it comes to jailbreaking devices, I do think the incentives will remain freedom-aligned. It will be hard to make devices the chokepoint. Maybe most people will end up having a cheap compliance-phone, for all services that require remote attestation, and a fancy free-phone. Though hopefully even the remote attestion will by made impossible by people consistently leaking these secrets.
We'll probably end up with an OAuth-like situation where the government (or some big corporation it trusts) has to approve every login attempt to gated services. But that at least keeps the alternatives within reach.