Hi Incog.
This was hard for me too. You can "see' the man in the hole if you stand in just the right place. Keep moving Simon around the front edge of the hole until you do and then you can talk to him. You need to use the yo-yo thing directly on the metal detector to get it. Since you don't actually "see" the metal detector in one the boxes, I didn't even think that action was possible.
Roz