I'm thinking about it from a cost / enforcement point of view.
PGP survived outright, explicit ban by the most powerful government with some of the most powerful cryptanalysis agencies in the world at the time not because "a company hid people's IPs". Your argument is: some users will be attacked for using applications for which lawyers have cheap attack costs/enforcement. It does not follow that, some agents being unable to survive their strategy results in an alternative strategy dominating.
Let's be real: legal systems that have the power to demand IP records subpoenas also have the power to demand logging, so you're argument that white-market companies can somehow provide anonymity, or shielding from culpability, to users doesn't hold water. One might interpret the outcome of the PGP battle happened because of some advanced concept like free-speech rights but the unavoidable reality is, attackers have limited resources and if the benefit is less than the attack costs, the attack won't survive.