@Mikkel ******
"he is already on yearly extension. He apply for the 60 day visit family extension, and then again a yearly extension." . . . . . . . YOU ARE WRONG! He will first need to apply for the "change of visa type" to a 90-days Non-Imm-O family visa, before he can apply for the 1-year extension. He cannot go staight to the 1-year extension from out of a 60 days family visit extension