Why don't we combine everything?
We get the tailors to line the pockets for dirt removal, and prepare something to dig.
try to get 2 scalpels, that means when we get to the northern gp, one very skilled guy can quietly kill both guards. Two more people go up, pretend to be the guards, the guns can go down and.. hmm.. not sure what from there,
we'd have to act quickly, but we do have two guns.