Milo is hilarious, well-spoken and doing good work by attacking third-wave feminism.
That being said, he is by his own admission not what we think of as a conventional homosexual.
Milo is, by his OWN admission, attracted to being taboo. He has a sexual desire to be in the wrong. If you listen to the Joe Rogan Experience with him, it's impossible not to see that most of what he does has to do with his need to be on the "wrong" side of the zeitgeist. I recall him basically saying he started to sleep with men just to get under his mother's skin.
He's a bit of a caricature. He is an interesting set piece in the political world, being the flamboyantly gay conservative guy. But he's a set piece nonetheless. His positions are calculated, as is his persona.