If we were living in normal times, Milo Yiannopoulos is somebody I'd do my best to know nothing about. However, given the melee at Berkeley, I decided to watch Tucker Carson interview him.
I think I first became aware of him during the Gamergate controversy. I also have some peripheral awareness of him in connection with Ben Shapiro.
From what I can tell, Milo is basically an opportunist. He probably values Dionysian freedom. Beyond that I doubt he has a serious political philosophy.
I'm guessing what makes him tick is that he's an aging homosexual. That fosters a carpe diem outlook. He's been able to tap into a segment of the youth culture, but his hipster appeal is threatened by the fact that once age catches up with you, that constituency will turn to someone younger and prettier. Age-wise, he's already at the outer limits of that market niche. Kinda like thirty-something actors who play teen dramas. You can only keep that up for so long.
What's mainly of interest is another front in the culture wars. It's not secular progressives v. social conservatives, but secular progressives v. the alt right, or manosphere, or overlapping groups.
It's a clash between different groups, all of whom are alienated from "traditional" values. To some degree, Christians are watching this civil war on the sidelines, because it's basically a fight between competing secular factions.
One dangerous development is leftwing goon squads got up in black fatigues like the Fedayeen, physically attacking people who show up to hear Milo, Ben Shapiro, &c. Why don't the police arrest them?
The alt right is a toxic mix of white supremacism and antisemitism, with a dash of chic Nietzschean rhetoric, yet it's no worse than the social justice warriors for feminism, transgenderism, ecoterrorism, euthanasia, &c. Pick your poison.