I'd assumed he meant more in the sugar daddy category by "special" - more relationships than just transactional sex, but who knows? I agree that reputation is a thing, particularly if you are playing at the higher end.
Good taste, in any case. If you're going to steal pics, though, tats are a mistake. Image search tends to fail miserably on white shirtless torsos unless there is ink or something else to distinguish.
Probably some ego, but that would be on both sides in that scenario. One thing I do think is that he might not be that experienced as a escort, if it really is meant to be a driver to OF.