I'd still rely on crowds directly rather than AI. I don't think AI is as accurate. You can post your photos on OkCupid and a crowd of people will rate them and help you select the best. Of course, you pay for this service by rating pictures of strangers.
At least with Gates it seems that him still being the wealthiest person on the planet has not much to do with his stinginess but with his investments that make money faster than they are giving it away [1].