New Rook is… different. Both his personality and past as well as his invisibility magic (or is it teleportation magic?) fit more with the theme of Shadowtown than Old Rook’s white necromancy. Just the same, I would enjoy seeing Old Rook make an appearance later, as long as you feel you aren’t forcing him in where he doesn’t belong (a problem I don’t think you’ll have).
As far as the restructured conversations, I like that you’re attempting to make the conversations feel more natural by having the PC offer their opinion on what has been shared with them