If there is any peeling — and there usually is somewhere — it's essential to scrape off any loose paint. This doesn't just mean the parts that are already separated from the wood and ready to fall off on their own. Each spot where paint has peeled loose needs to be scraped thoroughly until you can no longer get the sharp corner of a putty knife under any of the surrounding edges of paint. Then, the bare spot needs to be sanded until the paint edges are smooth.
This article emphasizes that houses exist in historical and neighborhood contexts. The author advises homeowners to consider what an older structure’s original color scheme might have been. She also recommends finding the middle path between copying the home next to yours and choosing colors that clash with it. This helpful list of tips even suggests a house’s natural environment as a color-scheme inspiration. Each piece of advice is thoughtful, yet the descriptions are brief and to the point.
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Every painting job develops a unique choreography as ladders go up and come down and tarps are unrolled and folded up. But two basic principles remain: 1) Start at the top and work down. 2) Work in the shade, out of the sun's glare. 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.)
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.
When painting the trim, you don’t have to be neat. Just concentrate on getting a smooth finish on the wood. Don’t worry if the trim paint gets onto the walls. You’ll cover it later when painting the walls. Once the trim is completely painted and dry (at least 24 hours), tape it off (using an “easy release” painter’s tape), then paint the ceiling, then the walls.