I’ve lived in San Diego and thought finding housing there was hard but it’s a cakewalk compared to the hell that is finding an apartment in Amsterdam. I’ve considered leaving the city at times because finding somewhere decent here that’s also affordable seems close to impossible.
Milan is bad but try Bologna where rental prices are now at Milan levels but which has more students, less housing and a recent tourism (AirBnB) surge. I got lucky, but I have student friends who were sleeping in tents in the forest for a while.