I'd definitely be down to play with Henry being Kieran's helper and I think the underlying tension angle could be super interesting. From Henry's side, he'd probably be fairly invested in earning Kieran's approval because he wants to learn from him and he sees him as an authority figure of sorts. But regardless he'll do his best and he'll be a reliable assistant unless the ol' bloodlust gets in the way and he has to excuse himself.
Jean. :))) Rob him blind. If she actually manages to take something off of him directly, he'll probably just assume he lost it and shrug it off. If she takes something from his wagon, he might get more wound up about it because he's protective of personal space. But regardless, yes please!