If you're preparing a home for sale, a buyer's inspector will typically flag the same warning signs covered in , and addressing them ahead of time, with a repair where that's genuinely sufficient, tends to be more cost-effective than negotiating a credit after an inspection finds them.
On the insurance side, as covered in , damage tied to a gutter system that was never maintained is generally harder to claim than damage from a sudden event. A gutter system in documented good repair, whether through targeted fixes or a full replacement, is simply a stronger position to be in either way.