I know it's subjective and I'm an outlier on this site, but cockrings, piercings, and especially tattoos are a huge turnoff for me. I want my men unadorned as god intended. (Big exception for Christopher Meloni!)
If I went to Burke Wiiliams I'd know I was going to get a massage in a clean space by a trained licensed professional. Diego might be cute but his ad says nothing about the room, his place, his training... so ultimately it's just a $260 hand job.
You're too generous. I think untrained guys advertise on rentmasseur so they can charge escorts rates for a lackluster massage/hand job. If they're into the client, the client gets an escort experience. If not....