Right, now that my essay is up to illustrate where I'm coming from, some more comments.
I like how you characterized your approach over in my thread---as 'pushing back' the fundamentals. This somehow seems very intuitive: the more general the mathematical structure, the less assumptions have to be made, and the less attack surface for 'But why this?'-type questions exist.
But does this process have an end? In some sense, you can always generalize further---throw away some more axioms, to put it starkly. When are we general enough? Is there some endpoint that does not contain any assumptions that can be rationally doubted---and even if so, does this say something about the world, or about the boundaries of our reason?
Exceptional structures seem to be good candidates for endpoints, in particular because they lend themselves to chains that actually do seem to terminate. Octonions are the division algebra with the highest dimension, things stop there---but then, why division algebras? E8 is the largest exceptional simple Lie group, but why any of that?
That said, I can certainly relate to the intuition that there's got to be some mathematical object of maximal symmetry, something ideally self-justifying, which---one might hope---gives rise to observed phenomena through some process of iterated emergence, be that symmetry breaking or multiple quantization. So this is kind of a point where I have my doubts whether the whole thing works---but would love to be proven wrong.