I do wonder how well blockchain-tech will fit within traditional regulatory schemes, if there may be certain core features of bitcoin that can’t be maintained under any imaginable regulatory scheme that would be acceptable to the US or any western country. Take the first issue you raise, short of a panoptical international regulatory/surveillance scheme there will be leakage of bitcoin to unidentified bitcoin addresses.

I’m a little reticent to commit to the idea that bitcoin is wholly antithetical to regulation, I remember the rhetoric from the early days of the internet, Barlow’s “you have no sovereignty where we gather…” And the internet was tamed, Post-Snowden the internet felt defeated even, but it’s not yet clear how the blockchain can be contained and our traditional freedoms maintained. It’ll be fun to watch.