Liberty is what sailors get when they dock. It usually involves boozing, fighting, and fucking. Freedom is what you were looking for I believe. As for the rule of law vs regulations, what's the difference? One is as illegitimate as the other when it comes to Free Men.
Moderation is necessary for a conversation involving many people. Regulation is necessary for markets involving many competing interests. Even in families, even in 1 on 1 relationships, there are rules. So there always are laws, guiidelines, rules, etc.
Having the rules in writing in my opinion is far superior than having then unwritten. Unwritten rules get enforced just as hard if not harder than the written rules. Unwritten laws also don't even give you the chance to learn what the rules are which you are being judged by. In essence you don't know the rules until you break it.
Considering that you cannot know how someone will react to something you say before you say it, if you have too few constraints on what you can say then your chance of upsetting a bunch of people rises. So how would you solve this without adding constraints and in effect reducing some liberty?
It's not ideal at all, but it's about maintaining harmony, quality of life, and preventing "mob justice" from being the ultimate arbitrator of disputes.
Think about it also from a consequence based perspective? Whether you agree with the rules or not, if the following of whatever the rule is, is more conventionalist than breaking it?
It's a matter of doing the cost vs benefit analysis for you as a freeman. In an ideal world we can change the rules but in many cases we can't and merely have to adapt our behavior to conform to the rules in order to avoid the negative consequence. Now if it reaches a point where you have a high probability of success at being able to change the rules, or if breaking the rules is more convenient, then these become favorable options too.
What is your opinion on the impact of surveillance, AI, social media, etc? These social media platforms can reshape social norms, morality, and laws, by renegotiating how people communicate, how people form friendships, etc.
If I form a gang and make a set of rules and if you don't follow my rules my gang will steal your property, beat you up, kill your friends, kill you and rape your corpse in front of your family before they steal and kill them as well. Whether you agree or not, is it more conventionalist to break them?
The cost is your freedom, the benefit is slavery.
Do you change the rules of the gang? If a gang is more lenient, do you change their rules? Do you have any say over the rules that people make? Can you change the rules of my house? What about your neighborhood, if enough of you gather, can you change the house of those that don't? What if their rules are to rape and kill you if you trespass against them like that by forcing them, who would be the Attacker and who would be the Defender? Who would justice punish and who would justice find JUST? Tired of all the hypotheticals pointing out that not only can you not change rules that you didn't make to being with, but just as you cannot tell people what rules they can and can't make people aren't any more justified in forcing you than you are in forcing them. If you consider people unable to be free, you must consider yourself a complete pathetic inexcusable slave, there is no in between, you are either Free, or you are a Subject, a Slave, you are either your Master or you follow another master, ultimately it's not a degree of freedom but only a binary, either you are free or either you are enslaved.
If you break some made up rules by a gang, does that mean anything? If I make up rules and you break them, does that mean anything? Can I say "you broke these rules, like it or not, where you agreed to them or not, and you owe me or you must pay"? Yes I can but people will look at my like a lunatic and laugh at me. It's no different if a gang does it, no matter how big the gang.
It's always the people and not the tools that are important. If we had nothing but censored facebook a whole language would form in the face of the tyrants and code would be imbued into every word, and I wouldn't fault facebook for censoring, but I would applaud the individuals who don't argue that it's a matter of cost vs benefit, but a matter of being free or not. Are you a Free Woman, or are you a Citizen, you cannot be both.
It's either LAWFUL, or JUST, or it's not. Law cannot compel performance, then it becomes slavery, there is no reason to limit what people can say, ever, words never hurt anyone, and there is no reason to tell people how to act, and neither you nor anyone is tasked with that kind of authority. Steer your own god damn ship and let everyone run amok on the rocks, they have free will and the sense of doing what they feel in their heart, and no Law will change that, such futility is embarrassingly stupid.