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You can paint an old wooden fence, but make sure first to do a deep clean (ideally with a pressure washer) and inspect the fence for any existing damage. Painting over dirt and debris will cause your paint to peel. Once you’ve cleaned and repaired any minor issues, use a primer and high-quality satin paint.

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. 

Regular staining, sealing, and inspecting for rot or insect damage prolongs fence lifespan.

The general consensus is that two coats of stain are required and since the cedar is siding, a third coat of sealant is always a good idea. This helps protect the wood and stain, so you won’t need to resand and restain for at least a decade. Each stain after the first will darken the wood, so be aware of that when choosing a colored stain.