Generally an issue like this is not a covered loss on a homeowners insurance. The reason for this is that it is a maintenance issue that should have been fixed by the homeowner before damage occurred. Now if a storm occurred and a tree branch broke the skylight and then because of the storm rain came into the home. In the second case the cause was windstorm. Windstorm is a covered cause on a homeowners policy and therefore not only will the skylight be fixed but also the damage caused by the water coming into the home and whatever damage was caused by this. Most issues that are covered under a homeowners policy and ones that are "sudden and accidental". A lack of maintenance type of damage is usually something that happens over a period of time.
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