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There’s no single paint that’s the most waterproof. Instead, there are several types of waterproof and water-resistant paints that suit different purposes. Epoxy paint, for instance, is commonly used to provide a waterproof coating to floors and decks. Masonry paint is an excellent choice for exterior walls. Meanwhile, there are waterproof acrylic paints that can be used for interior and exterior walls. It’s more about choosing the best type for what you’re painting instead of the most waterproof paint overall.

The general consensus is that two coats of stain are required and since the cedar is siding, a third coat of sealant is always a good idea. This helps protect the wood and stain, so you won’t need to resand and restain for at least a decade. Each stain after the first will darken the wood, so be aware of that when choosing a colored stain.

The best time to stain a fence is when the weather is dry and temperatures are between 50 and 90 degrees Fahrenheit. Late spring, early summer, and fall are typically the best seasons for this project. You should avoid staining during very hot weather, like in the middle of summer, or when it is raining. Heat and moisture can cause the stain to dry unevenly. Likewise, if it's too cold, such as in winter or early spring, the stain may not be able to dry fully. Before you start, check the forecast to ensure there will be no rain and low humidity for at least a few days.

Whether to brush or roll stain on wood depends on the project and your preference. Brushing is ideal for smaller, intricate areas and offers more control over the application, ensuring thorough coverage and penetration into the wood's grain. 

Conversely, rolling is efficient for more extensive, flat surfaces and can save time. However, it is not always the best fit for textured or uneven wood. Some projects may benefit from combining both methods, using a brush for detail work and a roller for broader areas. Ultimately, the choice between brushing and rolling depends on the specific requirements of your staining project.