Number two: Despite being based more on Florence and its history, I think Rome actually looks and feels more like Ankh-Morpork.
Number three: This statue of Machiavelli makes me think Vetinari. It's not a very good picture, but I know when I saw it I went "Havelock?"
Number four: Trevor, you fool! Read more Discworld so we can babble even more about it! >__