A quick further thought I had, regarding the Internet Oracle: What if I built a Jabber/AIM Oracle? You send it an IM with a request; you're asked, in turn, to answer another request; eventually you receive an answer after a period of Oracular ponderance.
Now, I've already found one impedance mismatch for chatbots, in converting an IRC-based bot to an IM-based bot. In particular, a privately-messaged automaton loses all of the shared context built up in a public chatroom. For infobots on IRC, often the users manual is found in watching how everyone else interacts with it. You lose that in 1-to-1 IM.
I'd imagine going from an email interface to IM would narrow the amount of context available, but would it still be a fun hack? Waste of time?