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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.

Vinyl can withstand many different cleaning methods, but there are two things you need to be wary of. First, particularly harsh chemicals will damage your vinyl siding and reduce its lifespan. Second, be careful about pressure washing your vinyl siding. Vinyl can resist powerful washing damage more than softer siding like wood, but high levels of pressure can still crack it. Use the lowest level of pressure for power washing vinyl, or hire a siding professional to do it.

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.

While homeowners' insurance can include coverage for siding, general wear and tear of siding is not covered. If your siding is rotting—especially because you haven’t kept up with proper siding maintenance—replacement siding will likely not be covered by your homeowners' insurance policy. Instead, insurance generally covers siding repair or replacement if your siding has been damaged by extreme weather, vandalism, fire, or some kind of collision, like by a vehicle.