I see it more as a soft trade-off, than something that has hard limits. The more I trust my own anonymity, the less I worry and care about the privacy at the other end. And the more willing I would be to give out details that could come back and bite me if my anonymity was blown.

I see it more as Stockholm Syndrome to the web’s client server model. People are willing to abandon privacy to a web server out of convenience but that doesn’t sound emotionally appealing so they give up and pretend what they have is good enough.