@Razzleg,
I share some of your reservations about Chomsky and it seems to me that he does wriggle out of the ontological argument for "deep structure" by attempting to discriminate between "descriptive adequacy" and "explanatory adequacy".
His importance of course is partly historical with respect to the demise of "behaviorism" in psychology, and it perhaps in that light (the problems of observing the observer) that we should assess his philosophical contribution. However, I also think he is important as one example of taking "language" as a key issue rather than "logic"and therefore he is within the orbit of other key players like Wittgenstein, Heidegger, and Whorf.
It is particularly difficult to "speak of the meaning of meaning" because it invites an infinite regress. That is perhaps why some writers, like Maturana have taken a deflationary view of the place of "language" in "cognition". This tends to shift the argument away from ontology to epistemology and towards the constructivist thinkers like Vico and Piaget. These two follow the phenomenological trend that started with Kant's critique of pure reason. We might speculate along these lines that "language" has something to do with Kant's "perceptual a priori's" (like "causality") combined with Piaget's view of an active versus passive perceptual apparatus.
And speaking of wrapping it up, I always find myself drifting towards the overview of "reality as a social construction" which we acquire and modify through "language". In that respect we are perhaps like fish trying to analyse water.
