I think you are going to have problems with divergences. In your example above with the double pole, you may parametrize the integral as $z=z_0+\epsilon\, e^{i \phi}$, for $\phi \in [\phi_0,\phi_0+\alpha]$. Then the integral over the arc is
$$i \epsilon \int_{\phi_0}^{\phi_0+\alpha} d\phi \, e^{i \phi}\, f(z_0+\epsilon\, e^{i \phi}) \sim \frac{i}{\epsilon} \int_{\phi_0}^{\phi_0+\alpha} d\phi \, e^{-i \phi}$$
Note that, unlike the case where you integrate above a closed curve, the integral does not vanish in general. When the integral does not vanish, the integral about a double pole (or greater, say, $n$) blows up as $\epsilon \to 0$ unless you go around a fully closed curve. (There are cases, of course, where the integral does vanish, i.e., when $n \alpha = k 2 \pi$).