My 80-year-old mother is booked BOS-PHL-FCO; the time at PHL is 5.14-6.25 p.m. This is on a friend's AA miles. Within a day of ticketing, I urged her to see if she could get a longer connection; what she got was a promise of wheelchair assistance. My main worry would be about a delay on the inbound. Is there some hope that they'll hold the flight for a wheelchair pax? If she's at BOS in time for one of the earlier hourly flights to PHL, to get on it does it call for the international MoveUp fee? The friend is arriving on another flight to FCO around the same time, then planning to rent a car to get away from Rome, and they'll be in Italy for less than a week, so a major problem if she doesn't make that flight.
This will be just after the alliance change. If she knows in BOS that she'll miss the connection, I see BA via LHR, which she would very much dislike. I don't see much of anything to make the trip that night if she missed the connection at PHL.