Ok, so the pic is faked, but that's not the point. Mrs Hawking is in the picture to show that Desmond never had a chance, he would always find Penny (shiny Penny) fall in love, ask her hand from her father, become discouraged, and end up pushing that damn button. So what is the Catch 22, I really doubt it's Charlie, or why would that be the book the parachutist bought, and not something Sawyer would be reading at the beginning of the episode. Something has changed with Desmonds timeline, his Fate, and now he has the opportunity to be with Penny again, but at what cost.
Penny has found the entrance to the island, and sent a subordinate to bring Des a message. We really don't know how much Penny has learned in the three years since we've seen her, but it's probably a vast amount of knowledge of the island, since she had guys looking for it in the Arctic.