To Daniel Wood's point about "status quo," you can use leading questions to break that up from the get-go; instead of asking, "How long have you been Hardholder," you might instead ask, "Whom did you have to kill last week to take over the hardhold, and what finally pushed you to take that action?" And if the Angel has been around for a while, "what was your arrangement with the previous hardholder, and how has that all gone out the window now?"

I dunno if I have any great advice, but that is a very intensely status-quo-y set of playbooks. I would be making a lot of effort to establish the contingent nature of everything, and trying to avoid players being like 'I've been here my whole life / I've had my establishment for 8 years / I've always worked for the hardholder' etc. I would ask lots of questions about how things used to be different, where they came from, very recent destabilizing events and/or opportunities that could feed into their ambitions (and the ambitions of NPCs, of course.)