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Need advice

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I am replacing the rotten beams and wood decking on my flat roofed garage and removed some of the roofing to do so. I have planned to build a pitched/sloped roof to help with the water drainage and snow buildup.

1. Can I leave the remaining existing roof down, which is covering only the back half of the garage and build over top of it or should I remove it entirely? (I’ve contacted several people who are experienced in this and they gave me different answers)

2. What is the best way to insulate it after the slope is done? (i.e. foam board, fiberglass, blown in, spray on) (Again, I’ve asked about this with the same people and have different answers)

3. How do I properly ventilate the new roof?

Thanks for any input and feedback
 
Not sure what you mean by that? The garage is not heated. I am installing a metal roof due to the amount of snowfall on average.
 
When the previous owner installed the roof and overhang above the garage door, he didn’t secure the roofing down very well so water eventually leaked through.
 

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