I found Greens function summing over repeated insertion of 1PI in Schwartz p.330: $$ \begin{aligned} iG(\not p)&=\frac{i}{\not p-m}(i\Sigma(\not p))\frac{i}{\not p-m}+\frac{i}{\not p-m}(i\Sigma(\not p))\frac{i}{\not p-m}(i\Sigma(\not p))\frac{i}{\not p-m}+\cdots\\ &=\frac{i}{\not p-m}\left[1+\frac{-\Sigma(\not p)}{\not p-m}+\left(\frac{-\Sigma(\not p)}{\not p-m}\right)^2+...\right]\\ &=\frac{i}{\not p-m}\frac{1}{1+\frac{\Sigma(\not p)}{\not p-m}}\\ &=\frac{i}{\not p -m+\Sigma(\not p)} \end{aligned} $$
It seems to use geometric series assuming $|\frac{-\Sigma(\not p)}{\not p-m}|<1$ from 2nd line to 3rd line. I can't understand how the assumption $\left|\frac{-\Sigma(\not p)}{\not p-m}\right|<1$ is valid for all cases.
If I understand correctly, field renormalization and mass renormalization are done in next page, such that $\Sigma(\not p)$ is 1PI of self-energy before field renormalization. For example, electron self energy up to $e^2$ order in dimensional regularization is $\Sigma(\not p)=\frac{\alpha}{2\pi}\frac{\not p-4m}{\epsilon}$. Obviously as $\epsilon \rightarrow 0$, $|\frac{-\Sigma(\not p)}{\not p-m}|<1$ doesn't seem to hold.
Can anyone explain how I can use geometric series in calculating Green's function? Or is it just divergent and can't I use this?
Also I don't understand the idea of 'repeated insertion of 1PI' because it looks like we can count on the loop effect in a very ordered manner, but I think we need proof to legitimate this counting.