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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.

The longevity of paint on wood depends on factors like the quality of the paint, surface preparation, exposure to elements, and maintenance. Exterior paint on wood surfaces can last 5 to 15 years or more with proper care and maintenance. Interior paint tends to have a longer life span, often 10 years or more. Regular cleaning, touch-ups, and addressing any issues like peeling or cracking can extend the life of the paint. 

Both a roller and a brush are effective methods for painting a chain link fence. A roller will make the job easier by ensuring symmetrical strokes and reaching the backside of the fence as well, which cuts down on paint time. However, a brush is often necessary for painting the base of the fence and near the posts due to its ease of reaching smaller spaces.

Pressure-treated wood lasts at least 10 years, but with the right care and treatment, it can last as long as 40 years. Painting the boards is one way to increase the lifespan of pressure-treated wood. The layer of paint provides extra protection for the wood against the exterior elements and insects.