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Rooftop Deck on Pitched Roof, is it doable?

Hello! We just purchased our first home in Dec 2016. We have a 2nd story walkout rooftop deck (20ft x 12ft) that needed removed because the underlying flat roof was leaking, causing water damage inside our home. We discovered that the water was entering in where the deck posts ran into the rubber membrane. We are interested in pitching the roof slightly to prevent standing water on the roof, then rebuild the deck without inserting the deck posts into the roofing material. Is it possible to build a floating deck on top of a slightly pitched roof? We have had several contractors come to our home, but none are willing to do the work. Do you have any suggestions for us on how to rebuild the deck the way we have envisioned? We had the membrane replaced as a temporary fix, but it was too cold to seal. We are currently "waterproofing" the flat roof with tarps.

Thank you! Jill and Matt Nohl, Omaha, NE

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