Whilst it is certainly true that Quantum Probability Theory (QPT) is an entirely different framework from Classical (Kolmogorovian) Probability Theory (CPT) (specifically because the event structure is non-Boolean and the random-variable structure is non-commutative), we can still identify enough formal similarity to borrow the classical terminology. In particular, we can still give a satisfying answer to the OP's main question, which in my reading is:
Is this random variable [i.e. Hermitian operator] in any way related to my ignorant definition [i.e. measurable function]
The answer we'll see is a resounding yes. The reason this isn't obvious is because physicists do not tend to express the QM formalism in a probabilistic language. So let's do that now...
First note that whereas the underlying measurable space in CPT has the form $\langle\Omega,\Sigma(\Omega)\rangle$, the underlying measurable space in QPT has the form $\langle\mathscr{H},\Pi(\mathscr{H})\rangle $, for some complex Hilbert Space $\mathscr{H}$ and corresponding projection lattice $\Pi(\mathscr{H})$.
Second, note that whereas we use a Kolmogorov measure $\mu$ to make the classical probability space $\langle\Omega,\Sigma(\Omega),\mu\rangle$, we use a Gleason measure $\gamma$ to make the quantum probability space $\langle\mathscr{H},\Pi(\mathscr{H}),\gamma\rangle $. (A result called Gleason's Theorem establishes the relationship between these measures and the conventional density operators.)
But what about random variables?
Here we need to be a little bit sneaky and note that when it comes to calculating probabilities in CPT, the guy doing all the work is not really the measurable function $X : \Omega \to \mathbb{R}$, but rather its inverse, considered as a set function (let's call it $\sigma$):
$$ \sigma: \mathscr{B}(\mathbb{R}) \ni \bigtriangleup \mapsto X^{-1}(\bigtriangleup) \in \Sigma(\Omega) $$
Specifically, if you want to calculate the probability of $X$ having a value in some subset $\bigtriangleup\in\mathscr{B}(\mathbb{R})$, you first pull that subset back into $\Sigma(\Omega)$ and then apply $\mu$.
In other words, instead of working with the random variable $X$, we can work with its sister $\sigma : \mathscr{B}(\mathbb{R}) \to \Sigma(\Omega)$, which satisfies the axioms of what's called a Set Valued Measure (SVM).
What's the big deal about this alternative formulation of a classical random variable?
Well, this formulation has a perfect analogy in quantum mechanics; namely, that of a Projection Valued Measure (PVM), which is a map $ \pi : \mathscr{B}(\mathbb{R}) \to \Pi(\mathscr{H}) $, satisfying some simple axioms analogous to the properties of a SVM (e.g. disjoint Borel sets map to orthogonal projectors).
But now we can employ the Spectral Theorem of functional analysis to construct an equivalent self-adjoint operator $A : \mathscr{H} \to \mathscr{H}$ for this PVM. It is the self-adjoint operator $A$ that turns out to be more computationally convenient for calculating statistics than the underlying PVM, which is more easily interpreted as a random variable.
I've left out a few details that you can easily find in any good book on functional analysis, but the main takeaway is this. You can express the version of QM traditionally taught in physics courses in more measure-theoretic clothes, and when you do, it is the most natural thing in the world to think of a density operator as a probability measure and a self-adjoint operator as a random variable.
(By the way, your assumption that QM deals in negative probabilities is incorrect. The Gleason measures this algorithm admits all generate ordinary probabilities between 0 and 1, inclusive, which are used to predict relative frequencies of experimental outcomes as per the standard Born Rule.)