My interpretation is that he had doubts about raising the price as substantially as they did, and he still questions it from time to time. His doubts are probably not to the point that he would insist on lowering them again. I'm sure he realizes that that would be perceived as capitulation.
Is Drew implying that he would like Corton to be cheaper?
I am not sure what point you think he missed. Given his track record, I think it's more likely that WE missed the point than he.
He also seems to be missing the point by quite a bit - seems more like the opposite, in that you can't do anything interesting unless you're small.
I think he's just saying that when Per Se charges $295 a head, it makes room for others to come in below than that, and still not seem egregious. He's also saying that he is rather amazed at places charging $150 a head right out of the gate, a reaction many of us share.