I 
really frakking love this set-up, but it is a bit complex, and I'm really invested in making sure everyone who plays has a clear idea of what's going on.  To that end, I have a few suggestions on how to preempt possible sources of confusion:
 
I know I already asked this, but I'm anticipating a bit of confusion over that "Speaks to the Outsider" phrasing.  Maybe a slightly different wording would make it more obvious that it's a characteristic, rather than a power in itself?  Perhaps "Chosen/Touched/Blessed/Cursed/Valued/Prized by the Outsider", "Instrument of the Outsider", "Outsider Affiliation", etc.?
 
Second, a few of the roles and items are a bit unclear, especially the ones with a lot of moving parts (I'm thinking of Demoted Assassin right now, but there are others).  Upping the word count on a few of them might be a good idea, as would formatting them in a way that makes patterns/parallels clear (e.g. that "Outsider" characteristic could appear as a "tag" of sorts: 
[Touched by the Outsider] or the like.  Regarding items, maybe include how the item is acquired next to each one (even when you're just repeating something already mentioned in the Roles section)?[DOUBLEPOST=1378834200][/DOUBLEPOST]
	
		
	
	
		
		
			Maybe it's because I"m not at 100%, but this sort of looks like it needs a flow chart, and a rock paper sciors lizard spock diagram.
		
		
	 
 
Ninja'd 
 
I really hope people are up for the complexity of this:  These roles are quite well-balanced, the interactions are 
very interesting, and a lot of these mechanics are pure genius (I absolutely 
love the radio broadcast---have I mentioned that?).