Libertarians are either naive or cruel. Somehow they all seem to have a condescending attitude whenever they write about thinkers of competing ideologies, but really it's their own ideology that makes the least sense.
Their first failure is believing that an unregulated market is a free market. That is not the definition of a free market. A free market requires symmetric information by all parties involved. An unregulated market does not require information to be spread to all participants, so it is not a free market.
Additionally, markets will never take into account externalities. Pollution and public health would greatly suffer if factories were able to pump their toxins into the atmosphere. Without some form of regulation, factors like these would never be checked.
Libertarians also think that any agreement by 2 people should be allowed. However, as any lawyer will tell you, drawing up agreements is very difficult and time consuming. There is a ton of paperwork involved in the purchase of a house, but all of those forms are standardized and governed by various laws. They are designed to protect both parties in the transaction. Imagine if both parties had to comb through each and every word to make sure that the other hadn't changed some wording to completely overhaul the document. It would be an overwhelming burden.
People also have limited brainpower. If every time I went to the store to buy some milk, it would drive me crazy if I had to check every label to make sure it was pasteurized, homogenized, safely transported, and every other imaginable factor in the safe creation of milk. Even if I did manage to get all of that information together, who would stop them from lying? Who would punish them if they did?
Somehow, libertarians think that other political philosophies are naive, when they are the ones who think that if there are no rules, everything would be fantastic. Well, at the dawn of mankind, there were no rules. If it was such a great system back then, why hasn't it lasted until the present day?
Libertarians might say that the rise of governments ruined the pure world that existed before. But if a libertarian world was unable to stop the rise of oppression, doesn't that also mean libertarianism wouldn't protect people from oppression anyways?
Of course, maybe libertarians don't care if oppression happens as a result. Often these types of people also think they're above average and would benefit from a society with less rules. In that case they're pretty much bullies who wish the teacher would go away so they could extract what they're owed by people "beneath" them. In any case, there's no reason to believe their utopia would lead to any better outcomes than those of other misguided idealists.
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