Example # 1 - The flashing has failed and now the wood is exposed
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Example # 2 - The perimter metal gravel stop joint has broken open
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Example # 3 - The flashing has failed and the wood is exposed
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Example # 4 - A shingle has fallen loose
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Example # 5 - A structural steel member has been mounted to the roof membrane by workers that did not know what they were doing.  The watertight integrity of this detail is riding on the effectivemness of some caulking which might last a year, at most.

Example # 6 - A roof top mounted heating and cooling mechanical unit was installed by workers that did not know what they were doing.  The roof curb hasn't even been flashed.  The watertight integrity of this installation is relying solely on some roof cement, which might last for...maybe a year at most.