Is $32,000 to repair roof and siding a fair price?

I'm a first-time homeowner and unsure about the process. My home is old and terribly damaged, requiring significant repairs to the roof and siding. The total repair cost is $32,000, covered by insurance except for my $1,500 deductible. I'm concerned about paying the contractor the full amount upfront, especially since I'm not familiar with how insurance payouts and bank endorsements work. I'm meeting with the contractor next week to understand the steps and plan to ask for proof of work. I didn't grow up with parents to guide me on these things and am relying on advice from coworkers and friends. I'm also a little confused about how the mortgage lender and escrow might be involved.