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The best time to paint gutters is when the weather forecast predicts clear skies and low humidity. High humidity will likely prolong dry time, and rainy or snowy conditions may ruin your hard work before it can cure. If you have no other option than to work in inclement weather, consider choosing paint with a faster dry time, like acrylic or latex, rather than one that takes a while, like oil paint.

Yes, you can paint a flagstone patio, but ensure you choose a durable latex paint specifically designed for outdoor use and heavy foot traffic. An elastomeric latex paint will fill in all the gaps and create a waterproof seal over the stone. Even the best products made for foot traffic can last for one to two years, on average, so be prepared to reapply paint regularly.

For painting your cinder block walls, you should use a 1/2-inch nap roller. Depending on the square footage you need to paint, you might need a 3/4-inch nap roller. Besides rollers, you can also use a paint sprayer if you have one on hand or want to rent one.

You technically can paint wires in a basement ceiling, but there are several important safety and code considerations. It's safe to paint non-metallic sheathed cable as long as the labeling remains visible. You can also paint low-voltage wires and conduit and junction boxes to help them blend into your basement. 

However, you should not paint damaged or deteriorated wiring is a fire hazard because it poses a fire hazard. The same goes for painting over high-heat wires that connect to heat-generating appliances or systems. Be sure to avoid painting multiple coats onto any wires, as that traps heat and poses fire risks.