When you have a close group of people you know, cracking all kinds of jokes including the worst and most shocking ones works because you all know what you do and don't mean.
When this happens in a public place where all people are strangers, you have no way of telling those who are doing it for the lulz apart from those who actually believe these things. For this reason public spaces where hateful jokes are allowed begin to attract the hateful people who otherwise can't find a home anywhere else because their hate is rightfully condemned.
And you can't tell when someone is telling the joke because it's shocking or because they're making fun of the people who believe these things, or whether the punchline is actually the bigoted statement within.
The statements go past simple "cringy but ultimately free speech" when they advocate and glorify violence against other members who are actively participating in the otherwise democratic act of having everyone speak their mind: the bigoted people are now actively discouraging the existence/participation of others in this equality by hurling violence their way.
Eventually people being bothered by these attacks begin to leave and in their place join more and more haters. And it becomes a breeding ground for those seeking to radicalize to start meeting normal people with lies and caricatures that turn them against minorities whereas there are none left speaking out against them.
So this kind of behavior is different from the usual "guerilla" gamer toxicity in that it organizes into a force that actively promotes cruel individuals.
If you are truly concerned about free speech then you should be concerned about the attacks against minorities that stifle their public participation. We have one minority trying to push all the others out. You can tell who the aggressor is because they're the ones on the offense with this kind of behavior.
And quite frankly, what all is there here that is that controversial? This stuff doesn't fly in a lot of online spaces. Rules against hate aren't controversial. What's your number? A caricaturizing joke? A well wish for the death of a group? An active call to exterminate a group? There eventually comes a point.
Your stance is naive capitalism where everyone is allowed to do everything without limits for the sake of freedom, including attacking others - because "the free market will sort itself out". The only result of such an arrangement is groups of bullies who gang up and start actively terrorizing everyone else.