Ask what the inspection found
Request a clear explanation of the affected area and the condition of the surrounding roof. Ask which findings support the proposed work. Photos taken by the contractor may help explain the scope, but make sure you understand how those findings relate to the recommendation.
Understand the limits of a repair
Ask what a repair is expected to address, what it leaves unchanged and whether there are other known concerns. Discuss the practical limits and relevant warranty terms. A lower initial price does not tell you whether the proposed work meets your goals.
Understand the reason for replacement
If replacement is recommended, ask why a smaller repair is not considered suitable. Ask whether the proposal covers the entire roof or one section and what alternatives were considered. The answer should relate to your property, rather than a general statement about roof age.
Compare options on the same basis
Request written scopes so you can compare materials, preparation, removal, cleanup, exclusions and warranty terms. Ask how additional damage would be handled. If recommendations differ substantially, consider another assessment and use the same questions with each contractor.