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I don't know if I would have the heart to ask him for any money unless it was substantially worse before. This is more of a fairness argument than a realistic argument. I don't know what to tell you and opinions will vary but in my humble opinion, I wouldn't pursue any money from a guy when my driveway was already damaged. I'd figure that normal wear and tear plus the added weight of a water truck were all it had left in it.
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