Milo occasionally makes a somewhat coherent point but almost always manages to do it in the most loving obnoxiously stupid way possible. It's cool that he tries to exist outside of the mainstream line of opinion but what the hell is the loving point if you're not actually reaching out to anyone and instead you're just jerking off in your own echo-chamber
The problem with Milo is that his points mean literally loving nothing because he only fronts movements and gets being ideologies if they make people mad and focuses the spotlight on himself. The only reason people don't think of him as a scum-sucking leech is because he was at the forefront of gamergate for awhile there and people think "The enemy of my enemy is my friend" is great advice
If backing Hillary was a divisive, polarizing stance, you would definitely see Milo doing exactly that. He's an attention whore, to say the very least.