The main problem with using this type of Turing Test on E2's search engine is that E2 doesn't have any concept of context. Furthermore, it's a bit schitzoid in that it cannot keep track of the conversational topic. The real pitfall with assuming that E2 is conversationally intelligent is that, conversationally speaking, it has the interactive capacity of a two-year-old, moving from topic to topic without any coherent flow. It's too constantly distracted by the new subjects that come up in the search engine to follow its own "train of thought", which ends up being more like a "train of thought wreck."
The best solution for this kind of problem, I think, would be for E2 to eventually have the capacity to perform boolean searches that extend into the bodies of write-ups. A node title alone may not have anything to do with the content that fills a nodeshell (as many of us know all too well). If E2 could parse or extrapolate a write-up's content and compare it the context of a searched phrase, E2's conversational accuracy would be more realistic- even comprehensible. Right now, though, it's like having a conversation with a young Robin Williams who is suffering from ADHD and is on crack cocaine.
Doing a Turing Test on E2 now, as it stands, will have peculiar results across the board, no matter how many different angles of attack you use. The final analysis from a psychological point of view will be woefully bleak, making it seem like E2 is either inherently stubborn, bi-polar, schitzophrenic, depressed, mildly psychotic and antisocial in the extreme or that it's just plain bonkers. In its current incarnation, E2 would be sent to a mental clinic if it was to be interviewed by a hardline Humanist psychologist. I'd bet even money on it.
And let's not even get into the various bots that work within E2's matrix, like the EDB, Cool Man Eddie and Klaproth. A shrink's take on those would be that E2 is suffering from MPD (multiple personality disorder) and would prescribe about a metric ton of thorazine for the patient.