Sure, but then the same could be applied for anything like big sporting events, concerts, etc.... I guess the question is what negative externalities of these types of situations are we willing to tolerate? (not "accept", but tolerate... obviously people committing property crimes should be prosecuted)

It sort of goes to the question of what negative externalities are we willing to tolerate for certain freedoms? For instance, I think it's reasonable to assume that a robust gun rights regime will sort of inevitably produce more gun violence. A system like Nostr that is highly censorship-resistant will probably allow for the greater propagation of "bad content," depending on your perspective (hate speech, CSAM, etc).

I think the clear-headed pro-freedom argument is that yes, these negative externalities exist, and we need to work to mitigate their harm to the greatest extent possible, while understanding that the freedom gained by society outweighs those costs.

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I don't necessarily disagree with any of that in theory, but on some level I think its hard to rationalize away what comes with a mass of people. I know guns exist, and its possible that I could get gunned down going to work tomorrow, but its a lightning strike event - I can't see it coming, and I can't fully wrap my mind around the odds, so I can go about my day. With online stuff, I can always walk away, mute, block, etc. I have some means of getting away from it. A crowd is something that I can see coming, and I have some reasonable expection that things can turn ugly, and when things do, I'm largely helpless. Its like having a bonfire next to the forest - I don't want to tell people not to have the fire, but I also shouldn't be anywhere near it, because it has the likely potential to become dangerous and I am powerless to stop it.

I think thats a human response to seeing a large crowd. Zombie movies wouldn't be scary if we weren't hardwired to fear large unruly crowds on some level. So with protests, I'm not saying they can't do it, but I am saying I don't like it, and I don't want to be anywhere near it when it inevitably goes south.

I would also say, I would have more comfort with large protests if I felt that those causing property damage were actually prosecuted. Some get slaps on the wrist, but do most? I dunno, I don't get that impression. You show me large scale proptery damage, regardless of the cause, and that quickly turns me against it, even if I agree with the majority of the issues being protested against.