Here are some pictures to put question in context..... No real soffit just new hardie board covering gap under and behind board gutter will be mounted to. I marked the outside wall header and know that I need insulation on top of that but should I push the insulation out to make contact with the hardie board. Or just like I need to make sure I am not contacting the roof decking with insulation do I need to leave that open for air circulation. I took one picture of the area with flash and one without so you can see that there are some openings that have not as yet been sealed with caulking on the new hardie board.