With a fairly leveled friend, you can do this, if you coordinate. Recommend you work clockwise around the fort, grass area, middle area, take ramp up, fort area, up to top and around there. This fills the first search.
Second search, repeat the first but go to top of hill for town area of fort and search there.
As far as searching... locate item you want to search, have friend distract nearby guard, THEN search. Dont search first, as it will draw the guard and make the process harder / longer. I've leveled up my doll about 6 levels walking people through this part of the quest.
Samuel McMalley lvl32
Zeppers lvl28
P.S. If im helping you, listen to me! You go running around chaotic, and ill leave ya alone in the fort
