I think I might need to replace the roof of my home in the near future. I just want to share my questions on how to go about it and if there are better ways to get good pricing/warranty etc.

Is it better to go with a big box store or just work with a small local company directly ? The big box store will in all probability contact the work out to a local shop, but the labor/material warranty would still be honored by the big box store. Is this Assumption correct ?

What happens if the small local company that somebody works with directly goes out of business in the next few years? Do they usually transfer the warranty to some other company?

Is it worth going through insurance if there is some wind damage etc. on the roof? How much would the insurance actually cover and would it be worth it after deductible ? ( $1500 in my case )

For a shingle roof, is it worth spending more to get ‘better’ shingles that supposedly last longer ? Do the 30 year shingles actually last for 10 more years as opposed to 20 year shingles ?