Re #2: US carriers have for years offered nonstop service to Rome,Milan and Venice. Delta tried seasonal JFK to PISA for a while, but ended up dropping it, so I will be curious to see how American does with not-so-far-away Bologna. United recently announced additional service to Italy, I think Naples from EWR.
this answer is for Cambridge Mike. I just came back to the States after living there for 8 months and I don't think it's terrible. It just gets extremely hot! In addition, all of the university students are gone so its less crowded (might be a pro for you but for me, I liked it when all the students came back in September).Edited: 10 October 2018, 14:30