Maybe not trying to make MRJ look any younger was on purpose, to make the relationship seem less rootable, more not-right. And I agree, the Hook/Emma parallels were nicely done.
And, yeah, I never got why sending Emma to jail was supposed to help her fulfill her destiny, as opposed to, say, telling her the truth. As a plan, it doesn't make any sense at all, since it does nothing to prod her toward Storybrooke. How were they to know she'd have a son who she'd give up for adoption who would someday come looking for her? They didn't. They were counting on her giving up crime and ... then what? How would anything she does afterward send her toward Storybrooke, except for the kid they didn't know about?
Dumb-ass plan. Dumb-ass dumb asses.