buybuydandavis comments on Harry Potter and the Methods of Rationality discussion thread, March 2015, chapter 116 - Less Wrong Discussion
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At least of the latter, see the "I laughed and I laughed when I realized you [Voldemort] had made a Good Voldemort to oppose the Evil."
Of the former, yes, I think he knew. See his over the top protestations of how he was oh so ever so completely fooled by Quirrell, had absolutely no idea whatesoever that he was Voldemort, and felt like a fool and a moron for missing it.
It does cast a different light on that time he asks Harry why Voldemort does the things he does.
Dumbledore's an over-the-top kind of guy. I got the impression that he was being genuine in his comments re: Quirrell; see for example his initial confusion when he sees him in the mirror.
On the other hand, I'm now pretty sure that he knew Harry was a Riddle instance, or at least something similar, all along.