Very opponent dependent imo. Really tight players generally aren't calling many EP raises with too many Ax hands and they're not calling if you bet without an Ace (or a set) for the most part, so betting the flop accomplishes little.
Against some really loose-passive opponents betting is fine because they'll call with worse and if they raise you can throw your hand away without thinking twice.
Against the vast majority of everyone else these spots just suck.
+1
i definitely think you should be more likely to c-bet OOP than you would in position, not only in a WA/WB spot but in most situations in general. a) it makes the hand much easier to play, and b) it balances your c-betting range a bit, which is more important to do when you're out of position.
in position with KK on an A-high board you have the option to turn it into a 2 street game (letting the flop check through). out of position you don't have that option, which means your opponent can put a lot more pressure on you
there's no definitive answer. it's probably one of the tougher spots in poker that comes up a lot, and it shows why being OOP sucks. if i don't think there's any value in a bet i will usually check and just try to make good decisions based on what i know about them, their value-betting tendencies,
bluffing tendencies, etc.. otherwise you're kind of just paying to avoid having to make a difficult decision (sort of like "betting for information"... the information is almost never worth what you're paying for it). but if you think they can call with worse -- namely draws, second pair -- betting has enough upside that it's usually best to do OOP
