How i understood the rule is that the expansion limit is a cylinder (due to the unlimited vertical expansion) of 36" diameter. If, at any point, your robot cannot fit in this 36" diameter cylinder, then you will be out of size. Assuming this, your diagram 1 would be the most correct, however that diagram is incorrect as while diagonally, it is 36", the rest of the diagram is not actually 36". (hope that makes sense)
During inspection, I would take the sizing tool fully expanded (36") and see if there is any way to touch both ends to your robot while it is in any reasonable configuration.
Yup, the cylinder explanation is the easiest to think about (in my experience). Another thing to add is that this 36" cylinder will always have its base parallel to the ground. This is effective even while climbing, So, no matter your robot orientation, the horizontal profile of your robot relative to the field floor (almost like your shadow) has to be fitting within the 36" cylinder.
Whoops, I didn’t even consider that. My mistake. But make sure to measure relative to the field floor now. I think in Tipping Point it may have been robot-relative, but now its field relative.