A particle's Green's function $G(\omega)$ is analytic everywhere in the complex plane except along the real axis.
Does it mean that a bosonic $G(\omega)$ is possibly nonanalytic at the bosonic Matsubara frequency $i\omega_n=0$?
Yes, it does. An explicit example: $G(\omega,k)=1/(\omega^2-c^2k^2)$, the Green's function of a phonon, is nonanalytic at the frequency $\omega=0$ or $\mathrm{i}\omega=0$ at the momentum point $k=0$.