In this thesis we study certain singular Sturm-Liouville differential expressions from an operator theoretic point of view.In particular we are interested in expressions that involve strongly singular potentials as introduced by Gesztesy and Zinchenko.On the ODE side, analyzing these expressions involves the so-called $m$-functions, often generalized Nevanlinna functions, who encapsulate spectral information of the underlying problem.The aim of the two papers in this thesis is to further understanding on the operator theory side.In the first paper, we use a model for super singular perturbations to describe a family of induced self-adjoint realizations of a perturbed Schr\"o\-din\-ger operator, i.e., with a potential of the form $c/x^2 + q$ where $q$ is a perturbation.Following the unperturbed example of Kurasov and Luger, we find that the so-called $Q$-function appearing in this approach is in good agreement with the above named $m$-function.Furthermore, we show that the operator model can be chosen such that $Q \equiv m$.In the second paper, we present a negative result in this area, namely that the supersingular perturbations model cannot be used for all strongly singular potentials.For a potential with a stronger singularity at the origin, namely $1/x^4$, we discuss the asymptotic behaviour of the Weyl solution at zero.It turns out that this function cannot be regularized appropriately and the operator model breaks down.