Look for signs of wear and tear that can include peeling paint, color fading, cracking caulk, and wood that is soft to the touch. Soft wood is a big indicator of water damage. Wood siding typically needs to be painted or stained every 4 to 7 years, while other types of siding can last as long as 10 years. The longevity of your paint job is impacted by the level of prep work done, quality of paint, and weather conditions it was applied in. Learn about the ideal temperature to paint your exterior in this helpful article.