I think A would work better, honestly. B wouldn't be realistic in the game, just my two cents but the Ranch is a professional organization and if a Snake was constantly getting in trouble, treating clients like shit, etc I don't see why they'd allow him to keep working there. Nicholas Stone, the manager of the Snakes, wouldn't stand for that kind of behavior for long. Plus the Snakes aren't allowed to work when they're drunk (there's a 2 drink limit when they're on the clock and they can't 'work' when they're off the clock) and there's a pretty strict drug policy, so I just don't think that premise would be very likely to fly unchecked for long.
I hope you decide to join up, it's a fun game with a ton of possibility. :)