I have seen posts through the roof before, but very few don't leak. I was at one home where they did not know they leaked until the insulation was so heavy the family room ceiling came down one night with a big boom.
I also don't think you want to use roofing cement under each sleeper. The wood and cement will move at different rates with temperature fluctuations. I would add either some 1 ply, or rubber roofing under each sleeper. Also fasten each sleeper to the house at the rear with steel brackets.
Is the deck as wide as the roof below? Can you come down the out side and fasten into the walls below to get your uplift security?

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Rick Sabatino
Sabatino Consulting, Inc.
Oak Park, IL