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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. 

While the answer varies based on weather, 10 a.m. is a good time to start painting. The dew will have dried, meaning there’s no moisture on the house, and the temperature will likely be moderate and the sunlight less direct. Starting mid-morning should also give you enough daylight and pleasant weather to work on the job for several hours.

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.

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.