So the only option is to arrange an in-person meetup with a random stranger from the internet so that they can gouge me with a gigantic markup or just rob me. This sounds terrible even if I have no beef with the government, but totally absurd if I am actually trying to hide money from authorities; for all I know, the person I meet up with is a federal agent or works with them.
I think you are trying to hard to make it seem infeasible or not worth it. The not-worth-it part may be true for most people but it is definitely feasible, especially with decentralized exchanges and websites that let you get gift cards with crypto or even dash which has a debit card. As long as you aren't in jail of course ;)
It's possible to create a self-executing contract on Ethereum that will automatically send a pre-agreed amount of ether when you make a pre-agreed online bank transfer. In other words, it's possible to have exchange between fiat currencies and cryptocurrency without any need for trust, except in relation to whatever risk there is for each counter-party to report the other for participating in that particular transaction.
You would use trusted hardware like Intel SGX to provide proof of untampered processing of a set of data. Town Crier already has a proof of concept on the Ethereum blockchain. This allows one to prove to a smart contract that a webpage served by a particular PKI certificate holder contains some set of data.
LocalEthereum.com is being developed too.