It depends on the condition of the roof. If it's wood shingles that are poorly maintained and have algae and/or lichen growing in them, then you're likely to get a lot of organic matter in the water, including this plant matter. If it's a modern roof where they are almost all composite shingles, then there probably isn't a lot sluffing off from them, though obviously anything that has fallen onto the roof (leaves, pollen, etc.) is likely to contribute, but this could happen from blowing directly into the pool anyway.
I don't think it's a seriously bad thing this guy is doing. It should be somewhat easy to tell if there's a lot of organic matter getting into the pool since this should significantly increase chlorine demand.
Richard
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