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The heaviest paint when dry is paint that has a thick pigment and additives like sand or some other aggregate. Oil-based paints can take the longest to dry because of their thicker pigments and higher densities, while water-based paints might be lighter when dry because the weight of the water reduces as it evaporates from the paint.

You should wait for caulk to cure before painting it. Silicone and acrylic latex caulk can take anywhere from one to 10 days to fully cure, and polyurethane may take 10 to 12 days to cure. Always follow the instructions on the label when it comes to painting over caulk because different types require different drying and curing times.   

When choosing paint for stucco, it's recommended to use a high-quality exterior paint specifically formulated for masonry or stucco surfaces. Look for paints labeled as "masonry paint," "stucco paint," or "concrete paint." These paints are designed to adhere well to stucco surfaces and provide durability and weather resistance. 

Opt for paints with good breathability to allow moisture to escape and prevent potential issues with trapped moisture. You may also want to consider paints with UV resistance to protect the stucco from fading or discoloration due to sun exposure.

A professional painter will typically prep the walls to ensure a longer-lasting, smoother paint job. Prepping the walls can involve scraping off debris or flaked paint, filling in grooves or nail holes, sanding, cleaning, applying a coat of primer, taping the trim, and removing outlet covers. You should ask your painter before hiring about their process to make sure it’s in line with your expectations and needs.