Replying to a thread only a month old doesn't count as a necro, right? Well, I'm starting up a group of AW newbies tonight, and here are the very general, playbook-specific questions I've been kicking around.
Angel: Where do you keep your stash? Do you ever need to transport it? Where'd you even get it? Who wants better access to it?
Battlebabe: You used to work for __________, right? Doing what, again – body guarding, gladiator shit, something like that? Why don't you do that anymore?
Brainer: This is some high-tech shit – you get it scavenging, or did you have to pull it off some poor dead bastard? You think anybody wants it for themselves, or wants it back?
Chopper: So who do you trust most in your gang – maybe Dog Head or Rum? I hear you used to trust __________ more – what happened there?
Driver: Nice ride – where'd you get it? Who do you rely on to keep it gassed up? When's the last time the back seat's seen any action?
Gunlugger: I hear you had to kill Zuzu a bit ago, am I right? Why's __________ still upset about it? Do you give a shit?
Hardholder: Did you start this holding, or take charge of it? Who used to be in charge or helped you start it? Who's your lieutenant?
Hocus: Why do these people follow you around, anyway? You could have your pick of the sweetest ass among these followers of yours – do you? If so, who, how many? If not, why the hell not?
Operator: (Any PCs volunteering to be on his/her crew? Then...) What's your obligation gig? Who's the most trusted NPC on your crew, and what'd they do to earn it? Who's been bugging you for work, and why won't you hire them?
Savvyhead: Who taught you this shit? They still alive? Who do rely on for tools, parts, power?
Skinner: Where do you perform? Who's your biggest fan?