Lev,
I came across your essay only after the end of the competition. Nevertheless, I want to tell you that I very much enjoyed reading your essay, because it meets many of my own thoughts. You are touching a couple of essential points. Let me comment only some of them.
On page 3 you quote Gell-Mann asking Seth Lloyd: "... But is there a mathematically precise way of quantificance of a bit?" When setting up "a fundamentally new scientific language" it can be helpful to see how linguists handle a language: They would refer to a bit as a "symbol". A symbol does not have any specific meaning. To give the bit a meaning we have to add the "semantics". A bit then may have the meaning of up/down, when referring to a spin, or particle/antiparticle, when referring to a particle. On page 7 of your essay you essentially say the same: "... each bit by itself ... is not meaningful without the question to which it provides a binary answer."
In the text above you suggest "to informally associate the term (information) with both "organization" and "structure". I am following a similar idea in my essay, where I describe "informational structures", resulting from bits that are described in a "covariant" way with respect to transformations of the semantic frame of reference. I think these structures correspond to what you call "a representational formalism," because "all data is being collected and processed in that form."
"This brings up the key question: How can we plan an experimental verification of the ETS formalism?" If you agree that my "informational structures" are somewhat similar to your representational formalism, then I can in fact offer you such an experimental verification.
"Finally, some of the other big questions are: How are the structs stored and retrieved in Nature, and what is the physical nature of instantiated events?" You will find a tentative answer to this question in my essay.
I very much hope you will have a chance to look into my essay and tell me your opinion, because you seem to be the only author in this contest who pursues similar ideas.
Best wishes,
Walter