The question is what is the analytic answer to the limit of the difference of integrals
$(I_{+\epsilon}-I_{-\epsilon})|_{\epsilon \rightarrow 0} =\int_{0}^{\infty}dx \int_{0}^{\infty}dy\left(\frac{e^{-\frac12 x^2-\frac12(y+i \epsilon)^2}}{(x-i (y+i \epsilon))^2}-\frac{e^{-\frac12 x^2-\frac12(y-i \epsilon)^2}}{(x-i (y-i \epsilon))^2}\right)|_{\epsilon \rightarrow 0}$.
This comes from considering the integral
$I_0= \int_{0}^{\infty}dx \int_{0}^{\infty}dy\frac{e^{-\frac12 x^2-\frac12y^2}}{(x-i y)^2}$.
By itself this is not a convergent integral, and playing around with it, it seemed to me that the divergence is logarithmic.
However, by shifting the y variable above and below the real axis there, one can find a slight alteration which should be convergent (I believe), given by the expression at the top of this question.
I'm struggling to get a clean working calculation for this, but the most reasonable ones seemed to give essentially $\pi$ .
Any idea if this is indeed the correct result and how to obtain it cleanly?
Too long for a comment
I don't think I can provide the asimptotics of the form of the integral you presented. The situation is complicated by the fact that the second integral has a singulariry at $x=y$. But if your goal is to get a regular part of $I_0$, it can be done by means of another regularization.
Let's consider $\,\displaystyle I_\epsilon=\int_0^\infty\int_0^\infty\frac{e^{-\frac12 x^2-\frac12y^2}}{(x-i y)^{2-\epsilon}}dxdy, \,\,0<\epsilon\ll1$.
Switching to the spherical system of coordinates, $$I_\epsilon=\int_0^\infty\frac{e^{-r^2/2}}{r^{2-\epsilon}}rdr\int_0^{\pi/2}e^{i(2-\epsilon)\phi}d\phi=2^{\frac\epsilon2-1}\Gamma\left(\frac\epsilon2\right)\frac {1+e^{-\frac{\pi i\epsilon}2}}{2-\epsilon}i$$ $$=\frac i\epsilon+\frac i2(1+\ln2-\gamma)+\frac\pi4+O(\epsilon)$$