I don't see libertarianism as being able to jump outside the (legal/social) system in quite the way described here. It is not an escape from "how much better society would be if we just made a rule...". It is, rather, a very specific implementation of that principle: how much better society would be if we just lived by libertarian ideals, private property, courts where we can sue for fraud and coercion, etc. And then, due to its failure to jump outside the limitations of systems composed of imperfect humans, it fails for the same reasons. People do not tolerate libertarian societies; they are not consistent with human nature. The extremes of wealth that tend to result, for example, are incompatible with human emotions of envy. People stuck in a libertarian society will soon try to change it to become less libertarian. This is the lesson of history.