For me the issue is more than how creepy, technically-legal is distributed, it's more about how creepsters/misogynists/pretty bad people use privacy and free speech as defense systems online, but how I as a progressive who believes in free speech fits that reality into my support of those ideals.

I guess I liken it to a blood diamond situation in that how the information was obtained and distributed is important and tbh freedom of speech should have limitations I think. Not everyone everywhere in all situations should have the right to free speech, I know this is an unpopular and fundamentally discordant with most progressive viewpoints. I should qualify and clarify that what I really mean is that anonymity and freedom of speech are just too dangerous in some situations.

Is what that redditor was doing wrong? IMO, hell yes. Does he have a right to be a pervert? Sure, if he doesn't act on those feelings. Does he have a right to share his obsession of nonconsensual photos (even those girls posted those photos of themselves) with online through reddit, and do so anonymously? Mmm...not so fast. Yes he should live with those consequences of being a grade-A asshole IRL, but how do we preserve anonymous online spaces from being expunged due to guys like this? Is it possible? Is anonymity impossible to maintain online? What would free speech regulation look like (when technically no illegal things are occurring?) I just think of corrupt govts that will use that as an excuse to crack down on dissidents.

"how do we preserve anonymous online spaces from being expunged due to guys like this?"

Is it even necessary to do this? I guess I'm of the opinion that if you believe something (whether it's homophobic, or racist, or sexist) if you really believe it, you should be willing to say so w/o anonymity. If you're a creepy pervert you should be so openly and not hide behind an avatar and if you really must do that, that's what Sims or RPG's are for. Besides, obviously nobody is really anonymous on the internet as it is seemingly quite easy to find out who people really are.

"What would free speech regulation look like" this is the more important and complicated issue I think and I really don't have a good idea as to what it could be like.