Several of his points boil down to "Tell me how special it would be to have me as an investor, so that I can tell you you need to accept a low valuation from me

Several of his points boil down to "Tell me how special it would be to have me as an investor, so that I can tell you you need to accept a low valuation from me." At least, I think they do. He might also just have a great desire to be flattered.