Roofing shakedown

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Q: We are trying to decide how to proceed on a possible roof repair. Our shake roof is a little more than 20 years old, and one roofer said he thought it would last five more years. A few years ago we had a handyman replace a row of ridge caps that were missing or broken. We noticed recently that some more ridge cap shakes were split or damaged, and we contacted a licensed roofing contractor to replace these. He only replaced a few ridge caps in each area instead of the whole row. He also nailed down some of the older caps that were split next to the shingles he replaced. We spoke to another roofer who said that it is not good to replace individual ridge cap shingles. He said the whole row should have been replaced. This contractor is going to take a look and give us a bid on replacing all the ridge caps. Which of these approaches is correct? How do we know when we need a new roof and what kind of repairs are needed to prolong the life of our shake roof? A: You'll know you...