No I agree with all of your points
I just don't think it would've mattered whether they did or didn't do a time jump, for those things
About the Pike flashback episode; I totally agree with you that if they wanted the audience to maybe possibly sympathize with him more, they should've done that episode earlier in the season
But, I do think they did it on purpose this way
I think in the end they wanted to show us this Really unlikable person, only to show later - when he's already at the point of no return - that he actually does have some layers to him? So in don't think that episode was necessarily meant to make us sympathize with him, but just to show where he came from. Am I making sense?
