House Wrap Not Fully Covering House Before Vinyl Siding

One would be to remove the siding wrap the house and then reside it.
House wrap not fully covering house before vinyl siding. To sum it up house wrap is a lightweight paper like material that is most often used to completely cover the house directly on top of the sheathing and behind the vinyl siding. Do you think that there are any other options. My question is do i install fanfold foam insulation over the substrate and then put housewrap over the fanfold or do i put the housewrap on and then fanfold over that and then vinyl siding any help with this would be greatly appreciated. Its primary purpose is to prevent air and water leaks that may have seeped past the vinyl exterior.
I plan on putting vinyl siding. What do you suggest that we do. My house currently has cedar shake which i m removing because it is in poor condition. The second would be to blow insulation into the walls.
My house was built in the 60s and doesn t have normal plywood sheathing. Generally a home s construction method dictates the type of house wrap if any a building needs. I am not re sheathing the house so i am unsure if a house wrap is needed when re. It has that old sheet rock like sheathing it s black i think it is exterior gypsum.
So blowing new insulation should not be an option. It seems that we have two options. Basically the walls right now go exterior gypsum tar paper like stuff foam board vinyl siding. If you re planning on a siding installation during the colder months look for a house wrap that remains pliable regardless of the temperature.