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Caulk will shrink. Take a hammer and lightly dent the area where the hole is so there is a slight valley for the product to fill and bit into. Then use exterior grade spackle or even better would be bondo as was suggested above.
 
In your own words, if you did that I would fire you and keep a days pay. Most painting contractors I know would fire you and keep a days pay. There is a way to do things with pride and then there is half a** things.
You got a point there. Spray foam is nasty stuff to get on the siding of your house and never leaves a paintable surface.
 
We have used regular car bondo on wood with no problems. Your car does a lot of flexing so if it dopesn't flex, it would crack going form summer to winter or from the shade to the sun.
 
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