[contravariant]

Unless I'm very mistaken adding onto the end of a string doesn't affect lexicographic order, so that's effectively [ab]*. The ordinality of [ab] is simple, it's 2, but the kleene star is a bit of an odd one, it's not quite exponentiation.

To reason about the kleene star it's a bit simpler to consider something like R^*n, where you repeat up to n times. Obviously R^*0 = 1 and R^*S(n) can be built from R^*n by picking an element of R^*n and appending either nothing or an element of R, here the element of R^*n determines most of the order and 'nothing' orders in front. For technical reasons the corresponding ordinal is (1+R) R^*n, which is backwards from how you'd expect it and how you'd normally define exponentiation.

The kleene star can be recovered by taking the limit, identifying R^*n with it's image in R^*S(n). Which also doesn't quite work as nicely as you'd hope (normally the image is just a downward closed subset, it's not in this case).

I think [ab]* is equivalent to something like the rational part of the Cantor set. Not sure if there's a simpler way to describe it, it's nowhere near as simple as 2^ω, which is just ω.

[contravariant]

Hmm, turns out this fails to be an ordinal because regular languages aren't well-ordered (except if you reverse the lexicographic order, maybe?). They are what is called an order type, and it looks like it should be possible to identify them with subsets of the rationals, if you wanted to.

Perhaps reversing the lexicographic order makes more sense, in that case longer tuples simply order last so R^* = 1 + R + R^2 + ..., the limit here is much easier since R^*n = 1 + R + ... + R^n is downwards closed as a subset of R^*S(n).

Then again in that scenario [ab]* is simply ω because it is effectively the same as just writing an integer in binary, so it is less interesting in a way.