It seems to me that in this loop he is still at that point more obsessed with the Tower and having that make his choices than love for Jake. Its not high morality of saving the universe but just that he wants to climb to the top of the Tower. Then at the end of the series he has changed to the point where he is willing to sacrifice his life and his quest for Jake, thats a big step for him and I'm betting his next loop will be a lot different, different choices because he is different.