I don`t think that would fit with Jared`s "they find peace" idea. Even if he just meant Sam, that wouldn`t be the cute, peaceful existance for even Sam that Jared obviously envisions.
Right now, I get the feeling it is a bit meta. The show is ending and Jared has been kinda waffling on maybe retiring from acting (save for guest stints or what strikes his fancy) and settling down with his family for a bit. While Jensen wants to have more family time but still also pursue acting, just not on a 20+ episodes network show.
So Jared with that headspace probably finds it poetic when Sam gets his lifelong (occasional) dream of a normal life. And Jensen finds it weird for Dean at this point in the show.
Since Jared said Jensen might be more worried about the "semantics", I literally envision, in typical Dabb fashion, a Series Finale that is 95 % of dealing with the crisis and then a final montage of white-picket-fence life that comes out of nowhere and hasn`t remotely been set up well for the characters.
And Jensen talked it over with Kripke who was like "hey, why not, think of the "peace when you are done" lyrics" and Singer who was like "whatever, I think it works". So he just shrugged and tried to make it work for him.