5:08 PM, Saturday June 20th 2020
I can't give you an official explanation as I am not that good an analyst. I can tell you what I found and it is consistent with your first point. Either object can be in front of the other until you decide and make the first intersection line. Once that is done the rest of the intersection lines must follow its lead. The lines you are drawing are on the plane of one object according to the shape and rotation of the other planes cutting into it.
In your two examples below "is either one valid" only the first one is IMO. The second ignores that the box is rotated further away from the viewer than the other. I think your idea of lines needing to be perpendicular is wrong as the angle the planes intersect in 3d space would need to be 90 degrees also. I think this is proven by your 3d model where it is pretty close to the first option.
It is a mind-bender, you really do need to look at the two objects and imagine they are real in 3d space then try and drawing along the planes of those imagined objects.
PS If you haven't already watch the video on this to see see examples being drawn.