Ah, and here is one of those questions. He's studying the picture critically, then shifting his gaze to the prison marked on the map, where Septus is pointing. 

"If he is dangerous as you say, by what he knows, knowledge alone, why risk bringing him back alive?" He wonders what Crowe might have that the Order is interested in. Why was he locked away and not already dead? Sometimes Rickard even forgot they had a prison, unbreachable or otherwise: it wasn't as if they had a reputation for taking prisoners. 
Curious, to let such a confidentiality breach live, considering the risks. Whatever riches they hoped to reap from the man must have outweighed the risks of him escaping again, or evading live capture.

Other than this tinkering curiosity, it seems like a fairly straight-forward plan to Rickard. It will be more dangerous than what they're accustom to, but he feels strangely comfortable with this. The Blasted Lands do not house the innocent. They are wilds filled with nothing but heresy and creatures that do not deserve life.