Sure, all of that is sound. My point is not that Shannon's is a bad framework for thinking about these things, it's rather that the proposition "intelligence is

Sure, all of that is sound. My point is not that Shannon's is a bad framework for thinking about these things, it's rather that the proposition "intelligence is compression" takes the abstraction for the thing itself. As you said, information theory is a powerful abstraction and it is a useful tool for thinking about things in a certain restricted fashion. The trouble starts when we forget that we're using that framework and begin to make purportedly philosophical statements about the fundamental nature of things in terms of a single theoretical framework. I disagree re: compatibility with the Investigations. In my reading the investigations are pretty much a refutation of the idea that to know is to have, like you said, some representation or picture of the world in terms of logical relations. In modern terms it is the same as stating that to know is equivalent to having particular neuron firings. I think the major point of the Investigations was to illustrate that our notion of knowledge is not some objective, universal thing, but rather it's highly contextual. In this fashion two human beings with totally different backgrounds and neuronal firings could both produce an "intelligent" answer to a question; it all hinges on context. To boil intelligence down to compression algorithms is to reject this contextually and put us back into the position of trying to establish objective measures for highly relative concepts. Even Shannon's concept of information is relative; I guess I'd be ok with a statement like "intelligence is the selection of an acceptable compression algorithm in a context" but on the whole it just feels...super reductionistic and probably not what a rigorous epistemology would ultimately conclude. Really, the proposition that ought to be made here is probably something more like: "in information theoretic terms, intelligence may be represented as compression"; this allows the theory to treat of the idea without reifying the theory.