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Staining a deck with a rag is typically a better option than using a brush, as it helps the stain penetrate deeper into the wood. However, both brushes and rags are best reserved for detailed work because using these tools on an entire deck can require tediously crawling around on your hands and knees. A pad applicator, sprayer, or roller are preferred alternatives to applying stain over the majority of a deck. Use a rag for railings and other detailed work, and let the wood soak up as much of the stain as possible before wiping away drips or pools.

Yes, you must thoroughly clean your deck before staining. If you don't, dirt, debris, grease, and mildew can get trapped between the wood and the new stain. This not only looks unsightly but also prevents the stain from penetrating the wood properly, reducing its ability to protect the deck from weather and UV rays. As a result, the stain won't last as long or look as good. Any existing mold or mildew left untreated can continue to grow beneath the new stain, potentially leading to wood rot and structural damage. Always wait at least 48 hours after cleaning for the wood to dry completely before applying 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. 

The staining or painting process involves cleaning the deck, sanding surfaces, applying a primer (if needed), and carefully applying stain or paint for an even, lasting finish.