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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.

While power washing isn't a requirement before you stain a fence, it can make the job much easier and faster while reducing manual labor requirements. The stain will not work if the wood is full of dirt and dust, so power washing, sometimes called pressure washing, is a fast and effective way to prepare the wood for staining. Remember that you need to stain or repaint relatively soon after the wood has dried so that there isn’t time for dust and dirt to build up again. 

Adding a second coat of stain to wood can even out the color to some extent, but it won't drastically alter the hue if the initial application is too light or too dark. It's more effective at enhancing the richness of the color rather than significantly changing it. Ensure the first coat is dry before applying the second.