I totally agree that there should be different answers to a lot of the same questions when asked by different people. And don't forget the fuckery.
"Jackabacka's the most vulnerable to you because he doesn't like to hit women. Thinks they're all fancy and shit, ha ha, am I right?"
"Well, for Brace, the biggest threat was Balls, because she's got the biggest gun and is kind of firing it around indiscriminately. But you, man, didn't you steal some chick Harridan was flirting with once? He's probably gonna single you at and try to make it hurt, yeah."
"Your best escape route, seriously, you gotta ask? You know they're here for Hope. Just don't stand between them and her, run a different way, they probably wouldn't even bother with you. Cultists, always obsessed with something, ya know?"
Plus, only people who ask the question get the bonus to the roll. Just because Brace has recognize that Balls is the biggest threat doesn't mean Hope's done so enough to capitalize on the matter. So there can be a reason for multiple people to ask repeat questions even if they're expecting the same answer, and you're not exactly robbing them if you just go "Yeah, same as before for the exact same reasons, ditch Hope and you're golden."