Re: OOC Thread I
As heavily as you want, mostly. The way I see it, when you're playing a character with monstrous Charisma and a huge Diplomacy bonus, the ability to get NPC to do what you want is one of the powers your build is providing you (alongside the highly effective ability to Gather Information you've already showed a lot), so in general, you'll be able to get anybody who doesn't have a specific reason to do otherwise to go along with your suggestions. They just need to make sense and not be against your target's nature or personal interests.
That said, the way you roleplay things matters; unless it's something that's tricky or difficult, if you can manage to approach an NPC from an angle they'd be receptive to, they'll go along with your ideas, although obviously when you're relying on yourself there's always a chance you could screw it up. But then, unless you had some mean to always figure it out exactly what somebody will and will not consider against their nature or interest, the chance for failure always exists with rolls as well.
Does any of that makes sense?