For Jensen to have to make peace with, or accept, or let go because he thinks he's too close emotionally, says to me that he doesn't think it fits with the character(s) or it takes Dean out if the final moments. Combined with the remarks he said he had to come to understand why it needs to be whatever way it's going to be, leads me to think it will be Dean being forced out of the hunting life in some absurd manner. I can see Dabb full on putting Dean in such a place that he can't hunt because he is physically and mentally unable. And rather than give Dean a heroic badass death, I would not be at all surprised for Dabb to him put Dean literally in an incapacitated state where he isn't even allowed to use his mind to save people and hunt things. Maybe he ends up as a drooling mess in the Cage after he is swapped out for Adam...again. And not because Dean is going to make a deal that saves someone but rather Dean will be punished by Chuck for refusing to kill Jack by making him literally irrelevant in any way at all. Dean might not even be able to remember his life as a hunter given what happened in Regarding Dean. Thus it ends with Sam taking care of an infirmed, incapacitated Dean which will make "dabrothers" (tm Aeryn13) fans go awww, Sam is now taking care of poor old Dean.
And that's how it ends. That's my actual prediction.