I am having some issues understanding the definition of real numbers as a Dedekind Cut. Firstly, a Dedekind cut is a set, not a number (namely, a set in which all its values are less than the value of the rational number q), so i don't see how can we proceed from that. Then, I don"t see the intuition behind defining real numbers as Dedekind, even as a starting point,but I think it comes from this first problem.
Just to make it clear, I don't see how $\pi$ is the set of all rational numbers smaller than $\pi$.
So I think a lot of your confusion stems from understanding how/why mathematics is formalised. Set theory is a very simple theory, from which we expect there to be no contradictions. Here's a lightly anachronistic account of why we may want this:
In 1903, Frege attempted to define arithmetic from simple laws; one of which was `Basic Law 5'. In a (rough) sense, he proposed that a set was defined by a property shared amongst its elements; a seemingly simple system. Bertrand Russel (see Russel's paradox) demonstrated that this actually leads to a contradiction, namely if we consider the set of all sets that do not contain themselves $X=\{x:x\notin x\}$. From there we just ask if $X\in X$. Either possibility leads to a contradiction.
So what mathematicians developed were various laws of sets, axioms (which we predict by raw intuition, but can never prove) that don't lead to contradiction. One popular one is Zermelo-Fraenkel (ZF) set theory. Here's the rub; since mathematics with more exotic ideas, such as real numbers, aren't immediately obviously not-self contradictory, by embedding them as sets, bound by the rules of (again for example) ZF set theory, we have a stronger reason to think that they aren't contradictory. That is why we embed them as sets, and define our rules on them using set theory (but not unless you explicitly do so; usually we accept that addition, as an example, just works).
So in answer to the OP, it doesn't really matter how we define the real numbers, so long as it is defined within our set theory, and that we can prove the same things with the same definitions. Of course there are always aesthetic arguments over why one definition might be better than another, but from a general perspective, most do not really care.