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You can apply waterproofing over paint, but you won't get as much protection as you would if you painted the surface with a waterproof paint from the get-go. Not all waterproofing methods are compatible with painted surfaces, and they may not adhere well. This is especially true if the paint is glossy, old, or flaking. Waterproofing sealers are primarily meant to be applied to porous surfaces, like concrete, wood, or brick. 

Yes, you can paint over old exterior paint, but success depends on the condition of the existing paint and proper surface preparation. If the previous coating is in good shape (not cracked, peeling, or flaky), you can paint over it with less prep work. However, for the most durable and professional-looking results, follow these key preparation steps:

• Clean the Surface: Thoroughly clean the exterior to remove all dirt, grime, and mildew. A pressure washer can be very effective for this.

• Scrape and Sand: If the old paint is peeling, cracked, or flaky, you must scrape off all loose paint. After scraping, sand the surface to create a smooth, even base for the new paint. Sanding is especially important for wood siding.

• Apply Primer: Using a quality exterior primer is highly recommended. It ensures the new paint adheres properly, improves durability, and provides a uniform finish. If you are painting a lighter color over a dark one, a tinted primer will help cover the old color more effectively.

Some brands offer paint-and-primer-in-one products for convenience. Taking the time to prepare the surface properly will not only increase your home's curb appeal but also help protect your siding and extend its life.

Penetrating sealer seeps into concrete pores to protect it from moisture and staining, cracking, and mold caused by water. This means you cannot remove penetrating sealers like topical sealers. The good news is that penetrating sealant doesn’t have to be removed before resealing, as most topical sealers must. Instead, you’ll want to buy a compatible penetrating sealant (often the same kind already in the concrete) and apply it. Always follow the manufacturer’s instructions.

The easiest and fastest way to remove paint from a surface is to use a chemical paint stripper to loosen the paint and then remove the paint using a paint scraper. You can also speed up the process by making the area as accessible as possible, which could include removing window sashes or taking doors off the hinges.