In the order of sharps/flats in a key signature, the comes after the A flat.

E flat
E sharp
D sharp
D flat

No sending a portrait in todays world would not mean the same thing. no i don't think that if the president sent his portrait it would reaffirm a relationship. todays perception of authority is anyone who can make a person do something out of force so sending a picture does not come out as authority it comes out as weak and unknowing.