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For the longest-lasting exterior paint, consider acrylic or enamel (oil-based) paints. Acrylic paints, including acrylic latex and acrylic enamel, are known for withstanding harsh weather and sun exposure. Enamel-based paints are also one of the most durable options available. While latex paint is common, it typically has a shorter lifespan than acrylic or oil-based options. The paint's finish also affects its durability; a higher gloss finish is generally more durable. For resistance to moisture and cracking, matte and satin finishes can be effective, while a high-gloss acrylic or oil-based paint offers a combination of maximum longevity and durability.

Yes, you can and should paint or stain pressure-treated wood to help prevent the boards from cracking. However, you must wait for the wood to dry out completely before applying any finish. Freshly treated wood can take weeks or even months to dry; a common recommendation is to wait three to six months. To check if the wood is ready, perform a simple water test: drip some water onto the surface. If the water beads up, the wood is still too wet and needs more time to dry. If the wood absorbs the water, it is dry enough to be painted or stained. You can proceed with building your deck or fence while the wood is still wet, but you will need to wait to apply the paint or stain.

It’s necessary for paint to completely dry before exposure to rain, and that drying time varies by the type of paint used. Oil-based paint takes 6 to 8 hours to dry on average, meaning that’s the minimum time needed between the last brush stroke and the first raindrop. Latex paint dries faster at around 1 hour, and acrylic paint is even quicker, usually drying in about 30 minutes. If rain is in the forecast, check the paint manufacturer's details before laying on a new coat. 

You can apply stain over peeling stain, but it’s not a good idea. Your old stain will get in the way of your new stain bonding to the wood, so you’re likely going to see the same issue again shortly after application. Your best option is to sand off the old stain and clean the surface thoroughly before applying new stain.