He has always been happy to say whatever it takes to appeal to any audience he desires the approval of, or feels he can manipulate.
Yup, no question of it. I remember well when he first showed up in KotakuInAction subreddit trying to make friends. They dug up his scornful comments about losers playing computer games quick enough. Still, he kept on it, mildly apologizing for that and making some endearingly pathetic attempts at playing games. People saw through it of course. Still, he somewhat succeeded.
his supposed commitment to free speech is merely a convenient carrier for his other desires
Here’s where I think you’re maybe wrong. A troll of his type (I hate how overused that word is, but I know no better ones) depends on free speech. He can’t have any of his smirking fun without it. You can want a good thing for a bad reason. Much as a weasel he is, he has brought attention to things that were widely denied — like the willingness of some “progressives” to set off fire alarms and make bomb threats rather than letting him speak to willing audiences.
Of free speech, I take the view that getting between a person and people who want to hear what he has to say, is censorship. It’s not necessary to argue over what “consequences” of his speech Milo deserved and did not deserve.
The tapes had been out there for years, and Milo’s had plenty of enemies, so why didn’t it happen before? I’m betting CPAC’s skill at opposition research.
In the end, it was his “fellow” conservatives who got him. And they got him the only way you ever gain a hollow win against a troll, force him to get angry over one of the rare things he genuinely cares about (yes, I think Milo’s hatred of pedophiles sticks deeper than his other hates).