Go with him. If they are going to approve him he will most likely have to have a representative payee and that will be either you or his dad. Unless big brother wants to do it. They wont give a 19 year old who is getting it for psychiatric reasons with a felony conviction their own check. Aint happening.
Also...I have always been at the appts. They always ask me the questions. Half the time they never even have Cory go in to see them.