While I was riggig a skeleton I kept parenting my empties and armatures to the same, wrong object. Eventually I discovered the reason for this problem. One must select objects in a view window and not their box representations in a schematic window.
Rigging a character can be a complex task. I prefer to lay out my boxes in a rough approximation to my character's construction so that I may select any object or IKA joint directly.
The dotted line must be around the object that will become the parent. However, the only selection sequence that will yield this result is if the selections are made in the view window and not the schematic window.
I'd prefer it if it were possible to select an object in the view window or it's box in the schematic window and have the same result. Selection consistency is one way in which Blender can become easier to use.
tends to precede
I did some hacking in the oops window to generate positions for oops datablocks.
But i got stuck because the current code doesnt specify from/to or parent/child relationships.
Basically i had the same goal as you requested, but this requires some more investigation...
It sure is a useful feature and i hope it gets added to Blender someday!