The most worrying thing is the SW can decide not to take "no" for an answer, and pushes the issue. Now, whether that's a "just messing with you" thing or a serious inquiry thing is up to each individual player to decide from the tone of the SW's VA.
I do see your point on this and in part I agree. Though to me a more worrying thing would be if the SW could take it PAST the inquiry and Force the matter. If it's just a matter of, 'You can bend your policy for me, can't you? No? Oh well,' then I see that as being benignly dodgy for the most part rather than malevolently dodgy.