Mike Ingle:
Cryptoanarchy will have arrived when you can openly _advertise_ these services and still stay in business indefinitely. Most of the things we talk about - even Jim Bell's assassination market - already exist, but they cannot be advertised. You have to go looking for them, at some risk to both buyer and seller. If the seller is visible enough for you to find him, he is visible enough to get caught.
actually "cryptoanarchy" has a lot of different definitions, and as an exercise, during at least on cpunk meeting in SF there was a roundtable discussion about what it meant to each person. the definitions did vary widely. the most optimistic view of cryptoanarchy would say that its early phases are already upon us in the crypto inside browsers and the govt paranoia and posturing. other more restrictive definitions would be similar to your own. another view would be that "cryptoanarchy" in the sense of people living in a society where they evade govts have already existed. in my view cryptoanarchy is a quite Machiavellian concept and I would suggest that there are strong parallels. TCM, originator of the term, is a bit mushy himself in his definitions and refuses to be pinned down on many specifics. however he has a pretty good paper out on the subject.
Currently the techniques of anonymity are limited to two: indirection for source anonymity and broadcast for recipient anonymity. We are more or less where crypto was before the invention of public key. You can gain security by spreading risk among multiple parties (key distributors for crypto, or remailers for anonymity) but you can't 'make your own anonymity' like you can make your own security with public key crypto.
A theoretical discovery is needed particularly in the area of recipient anonymity. Good sender anonymity and weak recipient anonymity leads to 'hit and run' behavior such as spamming email and newsgroups, but not to anonymous markets.
an encrypted reply block using remailers is pretty secure technology. the remailers are not all that reliable however and these reply blocks are always breaking; they depend on every link in the chain working perfectly. I've proposed having an anonymous pool in which remailers post status information when they successfully pass on messages, such info could be used to make the remailers more reliable, although possibly at the expense of having to buffer messages. has anyone set up a remailer that accepts payment right in the message itself? that would probably solve a lot of the economic problems, and it seems that the technology, i.e. digicash, has evolved to the point it would be possible to implement this. (note I am aware of c2's web page anonymous sending feature, but as I understand it the digicash payment here is not automated in the sense of being contained in the message). with the ability to include a payment in the message itself, you could pay "buffer services" that would be a layer of abstraction on top of the current unreliable remailer network and have much greater reliability. it seems to me the main proponents of "cryptoanarchy" tend to suggest a government structure is a completely useless construction. perhaps so but they would end up erecting othre systems to deal with the void they might not call "govt" but would have most of the features of one, imho. something "govtlike" is a measure of a civilized society, imho, hence my distaste in cryptoanarchy with its seeming naivete on the legitimate and crucial role of govt in a society. the specifics may vary between implementations, but imho in general something "govtlike" is crucial to civilized society.