in the strength/conditioning program, and another season on a winning team help his stock?

My best guess is that he's not going to get that 2nd NFL contract. So... take a bag this year and stay in Provo, then go to the NFL sign that first deal and then hope you stay healthy long enough to stay for 3 or 4 years.

All of these points are moot if he can get drafted in the first 3 or 4 rounds. If that's the case... then he should go asap.