Do not decide from roof age, one leak or one photograph alone. The useful comparison starts with the cause and extent of the current problem, condition of the covering and flashings, deck and framing findings, prior repairs, remaining compatible materials, moisture below the roof and whether a localized repair can restore a durable weather boundary.
Then compare written scopes: what each option fixes, what it leaves unchanged, code or permit implications, manufacturer and workmanship warranty terms, expected follow-up and the basis for price. A contractor recommendation, a building-code requirement, a warranty decision and an insurer's coverage decision are separate and should not be presented as one conclusion.