Things I would check is whether there is any step flashing where roofing meets the, (looks like T 1-11 siding). Unless it is applied over sheathing there probably isn't. The other place is how the T 1-11 is sealed to the front siding with the metal corners. That whole area looks like possibilities for water to get in. Is that asbestos or asphalt siding, or striated cedar shakes on front?