I had a long running minor leak around my chimney flashing which was
aggravated by last week's torrential rains in the DC area. A roofer
inspected my damage and estimated that he would have to replace 4
plywood sheets, the flashing, and the shingles, all for $1,200. My
insurance deductible is $1,000. So I'm vacillating whether I will still
have the insurance co. pay for this since the deductible is almost the
same amount as the estimate.

First off, is $1,200 reasonable for labor and materials for replacing a
4 - plywood section of the roof? Secondly, since this is a combination
of a multi-year slow trickling leak and a sudden rain event, will
insurance pay for it? If it will be a big hassle, I might as well pay
for it out of my own pocket.

Any advice would be appreciated. Thanks.