Is there any strategic or broader political-philosophic problem with the misunderstanding between what a libertarian means by "freedom" and what most people think of when they use the term?
This assumes that there is a difference between how liberty is used on one hand and how it is used on the other. And I think that there is a difference. The libertarian believes in liberty as a process or procedure and doesn't concern himself with the order or static end which developes out of the procedure. The commonality of people however, conceives of liberty as some end-state either politically (checks and balances) or morally (libertanism, conservatism). Therefore when we say "we want liberty for all" we either appear to favor chaos or we appear to favor a 50/50 division of freedoms (e.g. one half of the country has the freedom to be conservative and the other half has the freedom to be liberal). This is reflected in a growing meme that libertarians are "tolerant". However, it is not under the banner of tolerance or indulgence as such, that libertarians work but rather, we spend all our efforts to realizing a specific legal system as our ideal.
This I believe is a problem with converting people since we are not in favor of anything beyond a more consistent realization of the idea that the greatest good comes from the free competition of forces and yet, the ever-growing numbers of supporters are too focused on some particular realization of this competition and not on the competitive process itself.
Not all libertarians would agree with this:
The libertarian believes in liberty as a process or procedure and doesn't concern himself with the order or static end which develops out of the procedure...we spend all our efforts to realizing a specific legal system as our ideal...we are not in favor of anything beyond a more consistent realization of the idea that the greatest good comes from the free competition of forces and yet, the ever-growing numbers of supporters are too focused on some particular realization of this competition and not on the competitive process itself.
For some, the goal is a competitive legal system, i.e. any competitive legal system. For others, the goal is a competitive legal system operating on a very specific legal code. You could argue that the two are indistinguishable, but only if you believe that this very specific legal code will inevitably emerge from any given competitive legal system [of course, if you don't believe that, but you still want this very specific legal code, then you have the problem of trying to explain how to "guarantee" it will exist in a competitive law situation, absent a central authority imposing it]. And then there are some (or at least one - me) who don't think a competitive legal system is possible at all, at least not in the normal Rothardian sense, and advocate stateless monocentric law (which everyone else thinks is impossible). Then of course there are minarchists of all flavors, from ultra-minarchists to Paulite constitutionalists - I'd certainly include them in any definition of "libertarian."
From The Ultimate Beginner meta-thread:
What Libertarianism Is
What Libertarianism is Not
Libertarianism breakdown
What It Means To Be an Anarcho-Capitalist
"Argumentation Ethics"
When regular people (statists) are pressed to talk about what liberty means, they spout off some vague association with "freedom" and government that doesn't go "too far".
When libertarians talk about liberty, they're advocating a system of violent morals enforcement (law) with the end goal of a society which they expect to be less ruthless and barbaric than statist societies.
Minarchist:
"For some, the goal is a competitive legal system, i.e. any competitive legal system. For others, the goal is a competitive legal system operating on a very specific legal code. You could argue that the two are indistinguishable, but only if you believe that this very specific legal code will inevitably emerge from any given competitive legal system [of course, if you don't believe that, but you still want this very specific legal code, then you have the problem of trying to explain how to "guarantee" it will exist in a competitive law situation, absent a central authority imposing it]. And then there are some (or at least one - me) who don't think a competitive legal system is possible at all,..."
Yes, this is the distinction. The two are definitely not indistinguishable. The former generally abstains from attempting to arrive at concrete contents of law, while the latter generally attempts, and believes it is possible to succeed, in arriving at concrete contents of libertarian law (what you refer to as a very specific legal code). The most succinct rejection of this latter view was written by Hoppe in A Theory of Socialism and Capitalism, 1988, notes to Chapter 7:
"It has been a common quarrel with this position, even on the part of sympathetic readers, that the concept of human nature is far "too diffuse and varied to provide a determinate sent of contents of natural law."
Thus, there has been a subtle shift in libertarian thinking over the last decade or two, away from thinking in terms of a concrete, universal, libertarian legal system, and toward thinking in terms of market-driven or choice-driven law.
The problem with the notion or conception of a "competitive" legal system is that it seems inseparable from the every-day notion of competition, in which all players agree on a set of ground rules. But the "competition" entailed in a competitive legal system need not be tied to a previous agreement to abide by a set of rules of the game. The competition may arise because an alternate system or organization emerges which it is practically impossible for the existing system or entity to prevent. The cost for preventing this newly emerging system may be too high, and the benefits of preventing it too low, so that the existing system is forced to acquiesce in the emergence of the new system. Then, the "competition" between systems needs no previous agreement on a set of ground rules. People may choose between the various systems, while those who are engaged in the various systems have not previously agreed on a set of rules of the game.
"It would be preposterous to assert apodictically that science will never succeed in developing a praxeological aprioristic doctrine of political organization..." (Mises, UF, p.98)