This is one of the most enlightening texts I've read on the subject of freedom in the social sense. I wasn't aware of the term "dialectical libertarian" but, if understood correctly what it entails, I'm inclined to say that I too identity myself as such. Your reflection about hierarchical sets of values and the balance between positive and negative forms of freedom seems very reasonable and provides a sensible point around which this discussion might revolve. Well done!
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"Dialectical libertarianism" is the notion that freedom should be evaluated in terms of the whole system. A dialectical libertarian approach might conclude that a government granted monopoly with government price setting is more libertarian than that monopoly without that price setting. A limitation set on a special privilege may make the system more libertarian overall than the same system without that limitation. This is not, however, to say that the initial injustice (granting of a monopoly) is okay though. And formal recognition of the right to negative liberty without actually providing some degree of positive liberty makes society less libertarian overall.