We book 330 days out and were able to snag two seats up front from JFK to FCO for next May. If you have trouble finding available seats on a Friday outbound and Sunday for a return, consider Thursday on the outbound and Monday on the return. Good luck.
We were to downtown Milan last year and noted there is a train that runs from downtown to MXP. MXP is about an hour out of the downtown Milan area is I remember correctly.
I suspect that AA's plan to make seats up front available for frequent flyers will also depend on what happens to Alitalia. If Alitalia continues to fly with AF/KLM or LH as a partner, I would think it would be easier to obtain award seats.
Good luck.