I think that Ahsoka leaving the Jedi Order is a turning point in Anakin & Obi-Wan’s life. When Ahsoka left, Anakin’s courage to hope went away and Obi-Wan senses it. Obi-Wan does his best to comfort Anakin but at the same time he knows that he is never going to be enough to undo the damage done.
I also thought of something Stover wrote:
Oh, this is a redo of my old attempt: here yay
Oh, and still about that "heart of a chief, soul of a dragon" scene: do you think - in terms of character+animation analysis - that Hiccup looks more and more scared as Valka tells him who he is? Love reading your stuff, mate:)