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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.

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.

Moisture and rot are the largest threat to wooden fences. Stain can help your wood fence last 15 to 20 years, but only if you choose a stain with waterproofing qualities or add a sealant. Oil-based stains create a thicker moisture barrier than water-based stains, though both are mold and mildew resistant. You’ll generally need to re-stain your fence every one to eight years to get full protection.

Your tool of choice ultimately comes down to personal preference. Many DIYers prefer applying stain with a lint-free rag, but others stick with a paint brush or a roller. Wipe the stain and work it into the wood, working with and against the grain. If you’re applying multiple coats, allow the stain to dry for around four hours between coats.