One of the appeals of Milo types is they appeal to the people who wake up every morning and think, "wouldn't it be great if being a complete horrible asshole was really attractive?" He's seemingly* successful, with lots of money and sex (that he's gay also means he isn't a competitor for most of his fans), and he achieves it all by punching down while making it appear if he's punching up (trans college students actually run the country!). Makes being a bully sexy, heroic, and well-compensated.
Not the hero we need, but for some reason the hero that many people want.
*I say seemingly because I have no idea, but it's the image he projects.