Diagonal
A light in a dark place
If i go thief, maybe do a side quest to have him join up? It'll be actually much easier that way.
Dammit! Which one am I going to choose!? Outlaw or thief?
Sure, we can have a quest where the prince is planning his escape. Your character can be one of the guards or just an opportunist. As for the class, both are good choices tbh lol.