A copy was made of this picture. For some reason, perhaps for save-keeping, the picture ended up in one of Penelope's books. Penny owns the portugese version of Catch-22 because her staff speaks portugese. At some point in time Mr. Widmore selected the same book from the Widmore library, which includes Penny's collection, to give to Naomi Dorrit as a token of his appreciation during a meeting or business diner. The picture was never discovered while the book was still in Naomi's possesion.
The double/triple photo could be an incident similar to the one with Sayid's picture of Nadia. At the time the photo of Nadia was shown the actress playing her had not been cast so they used a stand in. Unlike with Desmond's photo, the episodes in which the photo and character were seen were close enough for the photo scene to be reshot.