I'm not familiar with Lebesgue, or "measure theory." If you have any
good links on them, I'd be interested in learning.
You are dancing around an area of advanced mathematics that you might
find fascinating.
Things you might google for are Aleph, countable, uncountable, 1-1
mapping, advanced probability theory, Lebesgue measure theory, the
different kinds of infinity, Georg Kantor, transfinite numbers.
rationals are like thin strips of celery fibre in a thick soup of
irrationals. Even though you can always find an irrational between two
rationals and a rational between two irrationals, in a very strong
sense, irrationals are vastly more numerous, and most definitely can't
be enumerated by a set of strings.
How do you quantify that? You do it by integrating over all the
rationals or over all the irrationals. The set of rationals is called
a set of measure 0, because when you do that, their contribution comes
out 0. Just how you do those integrals is called Lebesgue measure
theory.
The way you usually tackle the domain of knowledge is with first
calculation of finite probablities and combinatorics, then
probability, then the various types of infinity, then probability
theory over these various infinite sets.
You then wander around in Markovian processes (the things that turned
me on most since they are so much like finite state automata.) and the
astounding 0-1 law.
This is stuff I did not learn until after I had my BSc back when I was
studying it, so the books you may find won't necessarily be that
accessible. Mathematicians tend to go for brevity, and elegance, as if
they were constructing puzzles. They are not big on handing you any
sort of intuitive understanding.