1. Without a doubt, the worst thing Kina has done was sentence a Norn to a life of imprisonment in Pandemonium. While she knows it was cruel, she doesn't feel guilty about it. To her, it was justified since the Norn had sold the party out to the Baba Yaga and intended to leave them trapped in her hut for god knows how long. It's a permanent mark against Kina from a moral standpoint, but it isn't a choice she regrets. Jordeira has a long list of horrific crimes, but if he were asked, the worst thing he ever did was kill his sister. It was an act of mercy to save her from the torment being inflicted by his former master, Ariamis. In doing so though, his sister's soul was bound and consumed by the Nameless One.
2. Kina is a bit of a pack rat and carries a lot of things. She refuses to go anywhere without a bag of cosmetics and a change of clothes. Her engagement circlet is another must as it keeps her safe from fire, which she still fears to this day. The Mask of Lochoria is another essential, mainly because it's the easiest way of communicating with Iolond. Jordeira carries around a kit that he uses to maintain his body when he doesn't have access to magic. He keeps dried flowers and herbs in order to disguise the smell of undeath. He threads them throughout the inside of his armor and replaces them daily. The kit also includes a needle and thick thread that he uses to keep his skin stitched together.
Bonus: Kina, with her flair for the dramatic and costume-like outfits, would absolutely be a theater kid. Jordeira would be a goth, there's literally no other answer for him.