Firstly, let me say that I'm by no means a tor expert. It would be better if Roger or Neil weighed in than relying on my opinions.
I'm seeing this as a nightmare. If it isn't possible to disguise the
fact you're using or serving tor--and last time I did a tcpdump on my
outside interface, it stuck out like a sore thumb--doesn't that
undermine its usefulness?
I'd be willing to bet that In some
countries the very act of disguising communication is as criminal as
transmitting illegal payloads. In a similar vein, in some U.S. states,
the penalty for refusing to take a DWI test administered by a police
officer is often as harsh as the penalty for DWI conviction itself.
(And I assume you mean SSL could be used to
encrypt content, not the destination of a tor server.)
Right.
If connections could be posted in such public, mainstream, or embedded in innocuous ssl, that might prove well. Perhaps it could be retrieved from an anonymous proxy service. Quite simply, it seems that you have to launder the data and appear to be getting it from an innocent data source.
Two comments: (1) what's to prevent gov't agencies from detecting the IPs of the anonymous proxies by themselves using tor? (2) As I suggested above, I tend to think some countries illegalize the act of encrypting communication by its rank-and-file citizens. I don't know enough about SSL to know whether or not SSL traffic can be sensed by a third-party even if not decrypted. I would think so, however.
In any case, I can't imagine that none
of this hasn't already been discussed -- probably ad naseum -- by the tor community in the past. I'm sure if we search the mailing list, these topics will appear.