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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.

Applying a sealer or topcoat after staining wood is highly recommended, though not always strictly required. A sealer protects the wood from moisture, UV rays, and weather-related issues, which is especially important for outdoor surfaces like decks and fences. It also enhances the stain's durability, prevents fading over time, and gives the wood a cleaner, more professional-looking finish. For some indoor applications, a sealer may not be necessary, depending on the type of stain used and the level of protection needed. It's always best to check the stain manufacturer's recommendations and consider the wood's intended use and exposure when deciding whether to apply a sealer.

Wood stains last anywhere from two to five years, depending on exposure to the elements, your local climate, the type of stain, and the surface it’s on. For instance, vertical surfaces last longer than horizontal surfaces. Some types of woods, like dense hardwoods, will require a recoat yearly, as they are too dense for the stain to absorb. In any event, apply a recoat every 2 to 4 years. As for storage, a can of unopened stain can last up to 5 years, though results may vary.

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.