I think the explanation of entropy's blind spot is a bit off. It's not actually a problem for entropy if something is generated by a rule, you can calculate entropy for things like the continuous fractions for instance, with an easy rule to generate them for any particular number. Likewise for decimal expansions.

The real blind spot is that entropy is meaningless for a specific sequence, you can't really ask about the entropy of pi if you don't have a theory for how the numbers are generated. Sure if it is pick a uniformly random real number between 0 and 10 then both files have equivalent entropy, but sending pi is also vanishingly unlikely.

There's actually a more subtle way in which this is a blind spot, which takes a bit more machinery. You can define entropy for an ergodic system, which could be considered a kind of mathematical RNG. Now as it turns out this provides a way to generate something almost equivalent to a particular distribution except that this argument only holds for most starting points not all. A direct example would be how pi generates a perfectly fine random distribution of digits (we think) but something like 1/3 does not.

The thing that frustrates me about this argument is that there is no shortest program that produces pi. You need a computer to run it, which is massive non compressed data, or a human to calculate stuff, an uncountable amount of entropy.

I see that the irrational pi has a smooth distribution of digits and a file full of zeroes is compressible, but they are both sort of magically part of a world that does not run programs and thus not quite different in a practical sense.

Just my thoughts and sorry for the confusion.

Lately I’ve felt Kolmogorov complexity is an unfair measurement because it takes for granted your underlying programming language as treats it as zero cost. In theory you could create a custom language and embed the program as data and “compress” a large random sequence with a better Kolmogorov complexity for that specific language than Pi, simply by not exposing the ability in the language to even work with Pi. I think what’s maybe more interesting is when you take into account the work of Dr. Futamura and the idea of Jones Optimality and view things through that lens.