Roofer says there are 8 existing roofs on a 60-year-old property

[Logan Allec]

...and wants to charge extra for each one.  Property is in Southern California just outside the LA city limits--generally mild weather conditions.  I find it unbelievable that there could be these many roofs on a building built in 1955, especially considering that the previous owner (who held the property since 1997) did not put new roofs on (the roofer does not know this), but then what do I know.  Here is his explanation:

"What I think happens is you're out here in the sticks, and when people have leaky problems they just they just roof over it each and every time.  The flat deck was an ongoing problem, and to fix it each time they roofed over the top so by doing the math thinking every 6.25 years they would roof over the top until now."

Is this possible?  Is there any way to independently verify that there are in fact 8 roofs sitting on this property?

[Michael Clanton]

@Logan Allec, as others have said, it is very hard to believe that there would be 8 layers of shingles on any roof, especially if you think it would've been since 1997. Most roofers would not (or should not) install that many layers for several reasons: voided shingle warranty, accelerated shingle deterioration because of the layers underneath, and constant callbacks for nails backing out of the shingles due to the nails being too short to grab wood roof deck under all the shingles. 

The easiest way to roughly check how many layers of shingles are on your roof is to get a ladder and look at the edges of the shingles at the gable ends (if you have gables, if not anywhere will do) of the house. Theoretically, for a 8 layer roof, you would count about 9 layers of shingles at the edge. The first layer is called a starter and is only installed around the outside perimeter of the roof. Depending on what type asphalt shingle it is, the total thickness of roofing visible at the edges would be 2-2.5 inches or less for 8 layers. 

I would get on the roof with him and get him to show me exactly how he is coming up with that many layers, and if you're still not sure, get another roofing contractor to verify. Hope that helps!