I think he's done. It's a question of economics. Once the Pats want to reduce his $$, then it's Hollywood vs Foxboro. Even if Foxboro is more $$ now, long term, he's going to get to the point where Hollywood will far outweigh what he can earn in the NFL.
Let's say they want to bring him back for like 17m for 2 years. Then retire. He can go to Hollywood and earn, what, maybe half or a third of that in two years? But then it's year 3-5 where he can cash in. Plus health concerns. I think he's going to follow The Rock's playbook and make himself into a bonafide box office draw. He needs to go lay (pun intended) the ground work now and then cash in when he's in his late 30's and early 40's. It's a long term plan IMO.
That doesn't even weigh the social scene for him, and we have no idea what kind of pressure his GF is applying on him, one way or the other.
The wild card is Tom. If Tom can talk him into a couple years, and Bill gives him a schedule like Bavaro had, then maybe he stays.