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I've always heard good things about USAA.

How about contact USAA and see what a 'live' representative has to say?
I'm wondering if there is some other part of the home description that needs to be reviewed?

Ask the representative why a 50year roof must be replaced after only 15 years?

I'm having trouble with the 'felt goes bad' concept. As I understand it, felt is a synthetic fiber and a waterproofing agent matrix, and should last as long as the main roofing materials - under normal conditions. Normal conditions is that the felt is not directly exposed to the environment.

Perhaps ask for a USAA inspector to visit your roof?

As for checking for leaks -
It sounds like an attic visit is required. Look first for obvious signs of a leak: matted down insulation, discolored water marked wood and insulation, etc. Depending on your agility and the height of the attic space, and accessibility, you might be able to do this yourself?
Perhaps do a preliminary scan, then, if need be get a pro to look at it?

If there is insulation against the inferior roof surface, that's gonna be a PITA. I think I'd hire an inspector with tile/slate roof experience.

Can you get a drone to examine the outer surface of the tiles? Look for broken tiles, askew tiles, etc?

How about the fascia boards and trim around the edge of the roof? Can you examine that, safely? Binoculars, telephoto lens and photos from the ground?
Any decay, or discoloration?

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