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The number of coats you need to apply when whitewashing a surface depends on how opaque you want the final product to be. If you're going for a transparent, barely there look, a single coat or two may suffice. For fuller coverage, you'll want to use multiple coats. Another option is to use a less diluted paint to get a thicker coverage. 

You should stain both sides of your fence to get the full benefits. Fences often fall along property lines, so you may want to save a buck by leaving your neighbor’s side in the dust. If you do that, all you get is a slightly better view. Moisture and UV rays can still sneak in through the side that’s unpainted or worn down and damage your fence. Rot and rust will spread, even if you can’t see it from your side of the lawn.

Staining or sealing a cedar deck or fence is highly recommended to extend its lifespan and protect it from the elements. While cedar is naturally resistant to mold and mildew, it is not impervious to damage from moisture, sun exposure, splintering, fading, and rot over time. Applying a protective finish creates a shield that preserves the wood's strength and appearance, potentially extending its life by five to 10 years.

When choosing a finish, it's helpful to understand the difference between a sealer and a stain. A sealer sits on top of the wood, whereas a combination stain and sealer soaks into the top layer. Because it penetrates the wood, a stain generally offers better protection against UV damage and rot and lasts significantly longer. For the best results that also preserve the wood's natural color, consider using a near-translucent stain.

To maintain protection, plan on reapplying the stain or sealer every two to three years, either as a DIY project or by hiring a professional.

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.