It is so hard to predict now as I expected him to retire three years ago yet he keeps signing one year deals to stay in TNA. I really think that it is time for him though, he would be a very expensive performer especially since he performs a limited amount of dates and they could use that money more efficiently. He isn't really pushed that strongly anymore as a main contender as they have wrestlers like AJ, Anderson, Pope, Joe, Angle, Hardy etc. who will be pushed ahead of him and rightly so. He is just a bit player these days and at the money he is on he isn't worth it. He should retire whilst he is still alright in the ring rather than going too long like Flair, Hogan and Nash.
Plus he can then work a DVD deal with WWE and he might even be inducted by WWE in the HOF so again he can earn plenty of money from those two things to keep him happy.