According to Sus' writing on the box, Kishiro asked for these portraits to be drawn. Ken think Sus retrieved them in Naegi on one of this trips to Japan. Since Kishiro died in 1931, the portraits of his parents must have been made before then.
I think its says, As an American, I can sincerely say that I am worried about a future of a country that disenfranchizes itself. Not sure what the word says though.