Ask the insurance company how much they are paying for the claim and if not enough to cover the company you liked best, try negotiating with both the construction and insurance company.Even though the insurance is paying, treat it like any other contract.And you should know if they are removing the old roof or covering over, cost if base wood needs work is generally extra, like $50 per plywood sheet or is it included in your case, type of shingle, lifespan of shingle--you should get what you currently have, so if your roof is lifetime, so should your new shingle--etc.  

I was recently told metal roofing will bring a higher return than shingles.

For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch. 

Eitherway, to know best someone would have to climb up there.If you want to do this yourself, get some binoculars or a zoom camera and take pictures, specifically missing/broken/misaligned shingles.

It needs a new roof, $14000, large roof area and its steep requiring a special shingle, but then its a lifetime roof:). 

Look for 10 x 12 or 10 x 14 bedrooms and 8-9' ceilings, good stucco/brick, clean no/low moisture basement, average shingle roof, etc.  

depends if they can install the new shingles over the old (second layer), or if they have to tear everything off (repair plywood and add new underlayment & drip edges).

While most MA people recognize the traditional white plaster boiler asbestos and exterior shingles, also be aware of the pipe wrap and floor tile.

A few shingles replaced (tree limbs) and a insurance replaced roof after hail 5 years later.

But the 4 points and wind mitigation inspection report show it is membrane roof rather shingle.