I've seen a couple of articles saying that, logically, Peyton Manning should retire if he wins the Super Bowl. I think we all know that isn't going to happen.
However, does it make sense for Bailey to retire? I think it does. Think about it, the Broncos are to pay him, what, 10 million next year? That's not going to happen. They have too many FAs they need to pay off, including Bailey's replacement DRC. They will either cut him or ask him to take a major pay cut and accept a backup role. I don't think the money would be the deciding factor for him, he's played though some big contracts and loves Denver too much to take a bit more money elsewhere.
However, foot injury or not, his play isn't anywhere near what it used to be. He is his own harshest critic, and takes it very hard when he doesn't play the way that he knows he can play.
With that being the case I don't know if he would want to (or should) keep playing after winning a Super Bowl.