How much should I pay???
Well, you have to first realize if that kid falls off your roof, you are liable as the home owner for his injuries because more than likely he doesn't have a worker's comp insurance policy. And if he damages your roof or steps through it, or tears the gutters off on his way down, he's got no way to replace it, because as a teenager he probably has no liability insurance.
In all honesty, if you can't do it yourself, then it boils down to some things are best left for licensed and insured pros.
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