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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.

You should repaint your fence every 1 to 3 years, depending on the appearance of wear and tear. Weather and usage will factor into how often you should paint another coat on your fence. If you need to replace a few fence boards or posts, you may want to consider repainting the fence to help protect the rest of the fence as well as the new pieces against damage and deterioration from being exposed to the elements.

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.

An exterior paint job typically lasts between 5 and 10 years, though this can range from 3 to 17 years depending on several factors. The longevity is influenced by the quality of the paint and primer, the quality of the application, the local climate, and the type of surface being painted. For example, paint on wood siding may need to be redone every 3 to 7 years, while painted brick can last up to 17 years. Aluminum siding often needs repainting every 5 years.