This is a little hard to describe so please see the attached image.
Often times a model datum point is used to precisely locate a datum target. When a datum point is used the orientation of the target area and symbol is defined by the annotation plane. Sometimes in order to best show the datum targets in a combined view the desired orientation of the target area and symbol are not the same but there is no option to specify them separately so your forced to choose one. The request is to add an option to specific a plane (surface or datum) for the target area when selecting a point to locate the datum target.
When placing a datum target on a surface (no point selection) this works as desired because the surface defines the orientation of the target area and the annotation plan defines the symbol orientation.