Dear Conrad,
I just finished reading your essay. To the extent that you were able to be precise about relatively profound issues in such a short format, I think I agree with most of what you say. Let me itemize a few remarks.
1. Regarding the information/communication-theoretic point of view, I think it's ironic that the very theories (relativity and quantum theory) whose development and application brought to light the importance and universality of such concepts continue to suffer from failing to completely incorporate their implications. For instance, if modern computer science could have pre-dated relativity and quantum theory, I have no doubt these theories would be viewed in different ways.
2. At the end of your introduction, you state that you're not proposing any modification of GR and QM. However, as you know from looking at my essay, I believe that it's becoming increasingly clear that modifications will be necessary, and that the clues for which modifications to make come precisely from information and order-theoretic principles.
3. Regarding the contextual nature of measurement, you know of course about Rovelli's work. The "decoherence" view of measurement is closely related by attributing "collapse" to interaction with the environment, and there are attempts to refine this view further. (See, for instance Pullin and Gambini's essay in this contest. I asked them some questions about this, but haven't heard back.) I don't feel that I understand this subject sufficiently, but I don't disagree with anything you said.
4. In your section 3, you mention Einstein's original "vague" physical views and how his mathematical friends "reconceived them." I think that Minkowski and company may have let Einstein down to some extent, and that Riemann or possibly even Liebniz would have served him better had they been alive, since they possessed broader views and took fewer things for granted. "Lorentzian manifolds" represent a very specific (and hence limited) way of expressing Einstein's physical ideas that shackles them to a convenient mathematical formalism admitting a lot of nonphysical baggage. Just because this formalism happened to be available at the time, while information theory, category theory, etc. were not, does not mean that we should continue to be limited by it today.
5. You mention "two geometries" in relativity, given by spacelike foliations and light cones. More generally, if we drop the manifold assumption, there are two partial orders, one a refinement of the other, and as you point out it is the causal order (defined by the light cones) that is physically meaningful.
6. Regarding your section 4 on quantum theory, this is where things become more complicated in my view. This is because the version of quantum theory one chooses seems to matter if one discards the static background manifold. The questions of what an "observer" is and where it resides become critical. For instance, consider Feynman's sum-over-histories version (the 1948 paper). Feynman discussed summing over particle trajectories in Euclidean spacetime and thereby recovered "standard" quantum theory, with its Hilbert spaces, operator algebras, Schrodinger equation, etc. Feynman was able to take all the trajectories to be in the same spacetime because he was working with a background-dependent model; the ambient Euclidean space is unaffected by the particle moving in it. Now, if GR has taught us anything, it is that "spacetime" and "matter-energy" interact, so different particle trajectories mean different spacetimes. Hence, in a background-independent treatment, Feynman's sum over histories becomes a sum over "universes," with a different classical spacetime corresponding to each particle trajectory. His original version is a limiting case in which the effect of the particle on the spacetime is negligible. You can still make predictions in this context, but everything is tangled up with everything else; the transition amplitudes I discuss in my essay a priori depend on the entire universes involved, and it is hard to think about what an individual observer even is, except as some sort of approximation. There are also self-referential and free will issues involved. You can begin to understand why I said little about the theory of observation in my own essay, especially considering the length limitation!
In any case, your essay rates high in my opinion. I would be grateful for any further thoughts you might have on these issues. Take care,
Ben