I suppose I would ask Kalcephalos if it's stressful to be a dragon; boars, bears, all kinds of anthros would (I imagine) have their more primal equivalent. And all of them are surpassed by the ingenuity and often strength of their humanoid counterparts. So is there any insecurity or soreness in being the smaller (and potentially lesser in other ways depending on the lore and mythology) version of your ancestor/counterpart? Also, if he's just a baker, how is he so buff?
For Garret, I'd ask him what kind of smithing he specializes in (weapons, armor, tools, knick-knacks, etc), and if his answer is "everything", then what's his favorite kind of thing to make? What's the most expensive or difficult thing he's ever made. And finally, if he ran off into the woods, would he revert to a larger feral state like real boars?
For Arakarn, it'd truly depend on if he's a magical healer, but based on what I can pick up, I'll make that assumption. Does he only know healing magic, or can he remedy and help without it entirely? What are the different ways he can use his magic, other than healing that is? And is he bullet-proof like real bears?
A few of the questions were goofy, but I think that's how it should be. From the sprites alone I'm already excited. Can't wait to see how this turns out!