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

Sounds like a great plan. We took a similar trip in April 2014. We flew to Naples, had a transferelax.com driver take us to the Villa Gabrisa Hotel in Positano where we stayed for a week, then we took the train to Rome for Eastter where we had tickets to the mass at the Vatican. When you go to dinner at Campo di Fiore, try Hostiria Costanza. The food is great and it is in an old historic building. The building was part of the old Theatre of Pompey which is where the Roman Senate was meeting when Julius Caesar was assassinated there.