I think he should retire now. especially with him having good finances and most importantly, his health! I can understand not wanting to go out with a loss though. Maybe one easier fight, then a tougher/bigger one to finish things off if he does well in the first. Really he's fought everyone and all that was left was a Mayweather fight but he didn't beat Pacquiao so that won't happen. I do believe Margarito either shortened his career, or at least contributed to it not ending the way it could have.
I too agree that Cotto needs a new trainer, I'm sure he's next outing could be far different approach and make him good. I disagree he should retire, IMO Miguel Cotto still has something to be better than he is now.
Very wise to retire in two fights, he has everything set for life !! Even his own promotion company, Miguel Cotto promotions. What do you guys think of his company?