Using a small-time roofer for reroof

[Bienes Raices]

I was told by the insurance company that I need to get the current roof replaced within one month of closing. The plywood is rotten in some areas and also needs to be replaced. Someone has recommended a person who lives about 2 hours from here. He reroofed my friend's roof for only $2500 (for a 960 square foot roof area), and pulled the permit, so he is licensed.

I've had a roof repair done in the past on a different house, but never the entire roof. My only concern is that, since this is a one person operation, am I taking too a big of a risk that he may not stand by his work is there is a future problem? Should I pay more to go with a bigger company? Or should the fact that a permit has been pulled alleviate any concerns I might have about the quality of the work? thanks