I wasn't going to touch this because it bores me to tears, but I will just so you don't think that if people don't engage you it must be because they are autoritarians incapable of using their imagination to challenge the current system. The fact that I am not a lolbertarian doesn't mean I haven't carefully considered every one of your arguments.
The thing is I considered myself a libertarian about 6 or 7 years ago. And then realized that it is one of those ideas that looks pretty cool on paper and makes you sound smart but it is based on an incomplete, reductionist view of humanity. If implemented, the libertarian dream (especially the an-cap dream really) will make civilized society break down. Most libertarians eventually make it to this realization on their own, which is why the majority grow out of this phase by the time they reach 30. Hence the fedora tipping meme. We use it to laugh at people like an-caps and atheists because they think they are being incredibly smart and usually are just inexperienced.
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How do you reach this conclusion? Why do I believe libertarianism is a reductionist view of society? Because many libertarians and every an-cap I have met believe that individuals exist in a vacuum. They also believe that the sum of everyone's self interest will somehow produce an organized and healthy society on its own. They completely fail to see that humans are double-natured. Man has an individual dimension (like dogs or gorillas for example) and they do act on it about half the time, but we also have a communal dimension (like bees and ants) that seek to form highly complex societies in which the individuals get lost. To a libertarian that second dimension is interpreted as an infringement on the individual liberties, since communities do require individuals suppress their individuality in favor of the community sometimes. And doing so allows us to organize and create incredibly complex and successful societies.
Libertarians also believe transactions are not affected by customs and traditions. They believe the only one that can oppress people is the State. In reality people can oppress other people without the State's intervention. The State is useful in those cases as it will act as a barrier to guarantee that one person cannot take advantage of another. Another example of this selective blindness comes with customs. Libertarians don't see custom as an important factor within society. It is what makes them think that "two people can agree voluntarily on a contract, if you don't like it, don't sign it! but why make the State interfere and remove freedoms for the people?". The problem here is you don't understand customs shape interactions every single time, and some customs are incredibly unfair to the point that sometimes the State must regulate them. Same thing happens with power imbalance. To give you an example of this, people who own property have an advantage over people who do not. Everyone needs to live somewhere so landlords tend to have the upper hand. In most states in the US the custom is that the landlord will ask for 1st month, last month, and security deposit. Meaning that you have to give them 3 full months in order to be able to move into the apartment. Then, he can show the apartment to whomever he wants while you are renting it and he can even use his key to enter your apartment while you aren't there as long as he gives you 1 day notice. In my opinion this is incredibly abusive and I hate to sign leases like this. The State doesn't make it illegal for me to make the landlord a proposal to rent giving him only the security deposit and 1st month, and not letting him show the apartment until I am gone. I am free to do it. But guess what? No landlord wants to sign a contract like this with me, because even when it is completely reasonable and it is the way it is done in Europe and elsewhere, in the US this isn't customary. So nobody signs. And since nobody signs with me I need to suck it up and sign these terms or else I will be living in the streets. This is obviously not the worse case of this, just the example I came up with since I discussed this with another lolbertarian recently.
Another example of why lolbertarianism fails in practice is the fact that it considers that every individual is exactly equal and they are all good people. If you think everyone will make the exact same choices you will then it stands to reason that a completely free society will work. But guess what? Not everyone is like you, not everyone is good natured, or bound to the same circumstances, and people take advantage of situations when they can even if it will fuck others over. An example of this is rich young people with no roots like me. I am a nomad. Since I am a nomad and I have enough money to move wherever the fuck I want whenever I want to, I could go into any country, exploit circumstances that will give me an advantage, screw society over and then leave. The consequences of my reckless behavior will be shouldered by the laymen. People who don't have the same opportunities as me, who are tied to a job and a house they bought, who have a family to raise, and cannot move to a different place. They are stuck with the results of my shitty behavior. An example would be this: a person such as me but with 100 times more money could back a socialist candidate who plans to control the currency, donate millions to his campaign, have him win and then manipulate currency to make a shitload of money in the process. Society will be incredibly fucked after when their currency is worth nothing and their savings are halved overnight, but the rich nomad will have made a fuckton and he can then up and move someplace else with the spoils of this. Lolbertarian valhalla can't prevent society from these shit scenarios, and a strong State can.
I could go on and on about this and explain how a libertarian society would completely break down, but like I said it is boring cause it is going over issues that I consider to be tired and this post is already a boring brickwall of text that I doubt more than 2 people would read.
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