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.