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The list of what removes caulk residue includes rubbing alcohol. In some cases, rubbing alcohol can also help remove water-based caulk. However, old caulk or caulk that’s in layers from years of upkeep and projects might prove to be too much for simple rubbing alcohol and may require a caulk-removing solution from a home improvement store.  

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. 

Pressure washing is the best way to remove paint that’s already peeling from certain types of vinyl and aluminum siding and some masonry. However, if the paint is largely intact and not yet peeling, or if your siding material can’t withstand the pressure, you may need to use other methods, such as chemical paint strippers, a heat gun, a paint scraper, or sanding.

Some homeowners have luck using pressure washers, but this only works for old or weaker concrete sealants and with very powerful pressure washers. You’ll get better results by pressure washing water-based sealants. However, it’s worth trying on any sealant if you’re hoping for the least toxic, least expensive, and most DIY-friendly option. To try this method, rent or buy the most powerful pressure washer you can find and take several passes at the concrete, completely pressure washing the entire area. You may need to repeat the process multiple times to see results.