Deciding which paint to use has gotten much easier now that acrylic latexes have pushed oil-based paints almost to extinction. The acrylics offer superior performance (they don't harden with age, the way oils do, so they move and breathe without blistering), they don't mildew as readily, and they emit fewer VOCs, so they comply with new air-quality regulations. They also work over both oil- and water-based primers.
If less than half the old paint is left, however, it may be worth stripping it all off. Guertin gets rid of stubborn remnants using shrouded grinders (like the PaintShaver), infrared paint strippers (such as the Speedheater), or chemical strippers (like Multi-Strip), then smooths the wood with a course or two of sanding. When siding (or bank accounts) can't take the shock of a total strip job, Rich O'Neil, of Masterwork Painting in Bedford, Massachusetts, has successfully hidden rough, well-adhered paint under Peel Bond, a thick primer.
As the dance proceeds, keep an eye on the weather. Rain can wash freshly applied latex right off the wall, and a temperature dip below 50 degrees F two days after application can interfere with adhesion and curing and dull the sheen of glossy paints. (Latexes like Sherwin-Williams's Duration and Benjamin Moore's MoorGard Low Lustre are formulated to tolerate temps as low as 35 and 40 degrees, respectively.)

The BEHR PREMIUM PLUS Ceiling Paint 1 gal. The BEHR PREMIUM PLUS Ceiling Paint 1 gal. features a durable, acrylic-latex formula that is specifically designed for use on previously painted or primed interior ceilings. This spatter resistant formula minimizes glare and provides a mildew-resistant finish. This formula also maintains the original acoustical ceiling properties.  More + Product Details Close

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