Repair the power pole on the roof with roofing cement. This is how to seal the penetration of the power pole through the roof on a permanent basis. Even if you are installing new roof, this is a method. Some locales require some kind of flashing when installing a new roof, but this method will get you to the roof replacement. The roof in this video needs to be replaced 3 years ago.
There may be some wood and soffit damage from time gone by with it wide open, but we are not tending to that here.