Question for you?? Do you know that you can send a picture 2 ways via iMessage, You can send it from the message app iself where you hit the camera icon on the left and it takes you to the camera roll to attach or you can go to the camera roll and choose a pic, Attach it and write your message, have you tried both ways to try and isolate if you can send ir from one way or neither way both you and your wife which is the strange part to me.