Naples, Italy
Pros: great food, close to the Amalfi coast, great historical sites (Pompei, etc), pretty cheap for Europe, cheap short flights to lots of great places in Europe, the island of Ischia, the island of Capri, mild weather and not too humid in the summer
Cons: insane traffic and drivers (like nothing anywhere in the U.S.), rampant non-violent crime, poverty, trash everywhere, mafia controls almost everything, no one actually pays their taxes, lots of worker strikes, nobody in Italy knows how to stand in line properly