I am duplicating jpg images that are on a wall surface with the option key and move tool. When I move and duplicate I lock in the movement with the arrow keys.
The copy shows a bounding box but no image unless I move the object away from the wall. When I move the copied image back to the face it disappears again.
You might need to space the .jpgs a short distance (a fraction of an inch) in front of the wall. Otherwise the OpenGL renderer can’t tell which of two faces in the same plane to display. Either that, or the Move isn’t quite parallel to the wall, and putting the image behind it.
A further option is to draw a rectangle in the wall face wherever you want a copy of the image, and apply the .jpg as a texture to it. That way you don’t get what’s called Z-fighting (a shimmering or stripey effect where two faces are in the same plane).