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Wood siding requires an air gap behind it to allow water to drain out, and for air circulation and venting to allow humid air to escape and keep the material from rotting due to moisture. 

You should plan to stain or refinish your home's cedar siding every three to seven years to maintain its appearance and provide maximum protection, though some estimates suggest a range of four to six years. The exact frequency depends on several factors, including your local climate, exposure to severe weather like direct sunlight, rain, and wind, the quality of the initial stain application, the type of stain used, and the overall condition and quality of the wood.

For homes in harsh climates with high humidity and significant sun exposure, you should plan on staining as often as every three years, while those in milder locations may only need to do so every seven years. For the longest-lasting protection in particularly harsh climates, consider using an opaque stain.

If you are looking for a lower-maintenance alternative, you might consider vinyl or aluminum siding. While the initial installation cost can be higher, they do not require as much upkeep and can offer more value over time, especially in areas with excessive rainfall or high humidity.

You should install your cedar shake siding with the rough side exposed. The smooth side is less resistant to weathering over the years, and the rough side gives your home a more rugged aesthetic. The rough side also takes to paint better and ensures any paint job will last longer before needing to be redone.

Homeowners insurance may cover the cost of siding repair or replacement, but coverage depends on the cause of the damage. Most policies will cover damage from a covered event, such as a storm, wind, hail, fire, natural disaster, or other impact damage. Your policy might pay for the full or partial cost of the repair or replacement. However, damage resulting from age, general wear and tear, or neglect is typically not covered, and you should expect to pay for those repairs out of pocket. It is best to review your specific homeowners insurance policy for full details on what is covered, how to file a claim, and what documentation is required.