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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. 

There are several highly durable types of siding that you can build right on top of without removing it, with wood being one of them, provided it's in excellent condition. However, a common reason for siding replacement is to eliminate materials that are in poor condition, making installing new wood siding over old not recommended. Additionally, the cost of adding siding over existing siding can increase costs to between $7 and $13 per square foot.

Composite siding, with proper care, can last 30 years and sometimes more. Because its color has a tendency to fade, you might want to re-paint it every five years or so. Before purchasing composite siding, check the manufacturer’s warranty—you should have a long-term warranty to back up the quality of the product.

The best type of paint for vinyl siding is a high-quality acrylic latex paint, often labeled as '100% acrylic.' This type of paint is lightweight and adheres well to the vinyl surface, which reduces the likelihood of it peeling or flaking. For best results, apply two coats and avoid using thick paint. The color choice is also important; select a light color to prevent the paint from absorbing excess heat, which helps extend the durability of your paint job.