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Yes, siding orientation can affect a home’s resale value, but in what way and by how much really depends on the prospective buyer. For instance, some buyers prefer the more modern appearance that vertical siding offers, so having it can increase your home’s value in their eyes. However, other buyers prefer the classic, more common appearance of horizontal siding, so having vertical siding can decrease your home’s value in their eyes. 

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 vinyl is the less expensive option, composite siding has been known to be more durable than vinyl. In addition, because it is made from recycled materials, it is a more ecologically-friendly choice. Composite siding is also more luxurious looking and comes in a much wider range of styles and colors.

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.