Walking along the roof of the Cathedral is my favorite memory of Milan.
Here's a thought, maybe we fly into the North and stay for a day/night and then take the train down to Arezzo (3.5 hr train ride)? The plane ticket from Dallas to Milan are about $400 less and that's $800 for the both of us so it might make sense to save that money and see the lovely cathedral in Milan. If not we'd probably fly into Rome since it's also a few hundred less than Florence and maybe stay in Rome for a few nights? Thought? Should we go North or South?