Site Grading: how do you wrap the contour around a building

[WPTARE]

I can't figure out how to wrap the contour around a building. I've looked at the passing solutions by NCARB and other videos. I still can't figure out or come up with a system to wrap the contours around the building. Everyone is glossing over this part in the guides I've looked at.

How do you know which contour goes in the back of the building with that weird shape it makes and which contour is just a typical "/\" for the swale?

Also what's the rule for measuring straight contour lines (a+b) to determine slope minimums and maximums?