If you want to increase your odds of an upgrade on 9/25, consider routing BOS-JFK-FCO and take the train down to Naples. It's a nice ride. The JFK-FCO route is operated on a 777-300 with many more J seats. It's nice to be able to fly direct into NAP but the 788 used is limited on upgrades and people are buying the J seats. If your budget allows for either the PHL or JFK option, consider buying PE so you're at least guaranteed some level of comfort if the upgrade doesn't come through. Another added benefit of going through JFK is that you get Flagship lounge access as a Platinum, regardless if what class you wind up in. One final word - if you buy PE, you may get immediate cash upgrade offers to J. They may start high and go down or vice versa. You will NOT see offers if you put a mileage upgrade request in though. Pesky IT bug/feature with AA.