Hello All,
I am new to the fine homebuilding forum and I am going to start with a troubling question about insulation and ventilation. Attached to this post are a few photos of the situation I am dealing with. This house that I am working on is our personal home. The original house was built in 1954 with a Flat cold roof. The house was added onto sometime in the 70’s adding a new room. screened in porch and carport. The Carport had a wood construction wall, a stucco covered cinderblock wall, and a brick wall. I am in the process of inclosing the garage and insulating it completely. I am struggling with ventilation above the insulation in this garage. The original roof is a cold roof with tar on top so it would need to be ventilated, but above this roof, a gable was added to tie into the rest of the additions. This is uninsulated, so I am assuming if I insulate this ceiling, I need to ventilate, but if you look at the photos, there is lots of blocking that prohibits airflow and some mold that needs to be treated, Im looking on advice on if I need to ventilate and how to fix the current ventilation issues so I can add ceiling insulation. 
Thanks in advanced,
Will