The solution I found assumes that there are 3 basic cases:
First, the three unique center points for the two rectangle proceed upward (positive y direction) so the gap is either on the left or right of the connection. In my code, I had the corner points of the rectangle organized by their orientation to the left or right of the center point, so if the bottom rectangle's left point is below the top rectangle's left point, then the gap is between the left points of the two rectangles, otherwise the gap is between the right points.
Second, the three unique center points have a maximum at the center most of the center points, so the gap is on the top. The gap is then between the two points with the maximum y values.
Third, the three unique center points have a minimum at the center most of the center points, so the gap is on the bottom. The gap is then between the two points with the minimum y values.
[I'll post pictures of the example cases if it is requested]