You could set up your own kind of certificate-style trust mechanism for the darknet, where you list people who you trust and only deal with those certified by these trusted parties (a highly decentralized version of certificate authorities for SSL, more for certifying trustability than authenticity though). Anonymity makes trust an absolute bitch to handle, but you can still corrolate trust. If a high volume, trusted vendor on Silk Road decided to start up a marketplace (and used PGP or similar to verify their identity) then you'd be a lot more confident than random new hidden service.
A bit beyond the scope of this project, but it's a cool thing I wouldn't mind getting in to!
Actually, that reminds of the Freedombox. Are you familiar with it? It's a software stack that's supposed to run on a plug computer and provides various services (email, blog, social network) in a privacy-respecting way (distributed, versioned, encrypted back ups, etc). One cool proposal they came up with was in backing up PGP private keys securely. You could select say 5 or 6 (or 20 or 50) trusted friends and send each of them pieces of your private key. They would all have to collude to pwn you, which presumably they wouldn't because you selected people you could trust. If you lost your key, then you contact them, and after they verified who are you, you could reconstitute your private key. Voila! Distributed trust.
That would be more difficult in a truly anonymous network, but it sounds similar to what you were saying. I know you were talking about the web of trust model.