When a home inspector looks for leaks, where pipes and vents exit the roof, it can be a subtle process. If there is an accessible attic, the inspector will try to look around these appurtenances (big fancy word for stuff coming out of the roof). Another method, done in virtually every inspection, is to look at all of the flashings on the roof. Is the metal rusting, is the flashing done right, are the shingles or roofing around it holding up, has debris collected that blocks the flow of water?
The defect in the photo below was an easier find than what is normal. This is a view from below, in a garage. Look to the sky, at the left side of the vent. That white spot is the daylight above. Since that showed up, even with my flash, you can bet that was a pretty large gap. Also, it was a gap that was very friendly to water intrusion. This was an easier defect to find than what is typically the case.
Steven L. Smith
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