Well, since Dareios is mayor now, he doesn't handle a lot of his business directly anymore. He's always known about the Ark's dealings, but have mostly stayed away from it and done his own thing. Since he's mayor, it seems out of place for him to just stop by and ask... that would be something he'd have the police do. So I don't see him poking around in someone else's illegal business right now. Though if they met completely at random (unrelated) he might be curious enough to see what kind of information he could get out of her indirectly...

Would Raven be involved in anything else? Neighborhood stuff that would bring her to a local gov meeting or directly to the mayor's office to complain about something related to the city? Or is she friends with any vampires? Dareios is on friendly terms with Islot and the lot at Red on the Water, but I'd say they're mostly just acquaintances.