stages of rebellion

[LostSoul]

You might want to get a third party to role play the Prince for you. In complex open-ended scenarios like this, I find that's interesting way to remain the "referee", without being tempted to have the enemy be either omniscent about the PC's plans, or giving them too much of the benefit of the doubt.

That's one of the reasons I think a skill challenge would be handy.

Then again, I played a lot of Burning Empires, so I'm used to that sort of thing.