what if he always routed through an encrypted tunnel to a vpn?
The goal of encryption is to prevent an eavesdropper from reading messages, not to prevent them from tracking their source and destination.
Transmission Control Protocol (TCP) – and – as far as I know – any other connection-oriented protocol – connections carrying encrypted Application layer payload are – for content-irrespective tracking purposes – no different than ones carrying unencrypted Application layer payload.
You've made a point that I've made before. Sending encrypted data is sound a horn, hey look at me. That's why you send your grocery lists in encryption. Sending visible encrypted data that appears as non-encrypted data sails by without notice. The down side is the time for encrypting a 'non-ecrypted' message can be lengthy. Time is an enemy of cryptography. If you can't encrypt it fast enough, it's useless usually. Same with decrypting, if it takes you 10 years to decrypt a message, the original message is useless.
Deterministic OTP's can be very useful. The base (any easily ready material, Bible, PowerBall, etc...) can be used as a base for creating an ∞ amount of OTP's
One Time Pads are proven to be uncrackable. Except the Rubber Hose technique, but even then a OTP could decrypt into many messages depending on how it was encrypted. Rubber Hose decryption = "Nixon did it", and the real decryption = "Obama did it".
