re: Two weeks in Italy. Tell me pros/cons of what I am thinking already...

Maybe consider swapping Positano for Cinque Terre? Just a suggestion based on logistics. Florence to Naples will be a hike. Or, pull a day from Positano and do something wine related while you're in Tuscany.

Highly recommend following the Rick Steves book. His walks are pretty easy to follow especially if you're staying in a central location. We stayed near the Jewish Ghetto and everything was walking distance (Xenia Guesthouse if you're curious, it was a wonderful hotel). Also, the Jewish Ghetto is one of the better food scenes...there is a little street right off Via Arenula with a burger joint and then 4 or 5 restaurants (Giggetto is one that is supposed to be excellent). I also highly recommend another restaurant off of Via Arenula going toward the Campo di Fiori, it's called La Regola and is in a very small and quiet church square. Food is excellent as is the service - very friendly and excellent English.

I also agree on the Firenze card. It's around €70/person but I think if you plan to visit 4 museums/churches it pays for itself or comes close and you can skip the lines which is a huge added bonus.