Inspect the surface area for holes, cracks or other problems and apply acrylic caulk to fill them in. Use a putty knife to smooth out the caulk and remove any excess to prevent bumps. For particularly thin or narrow crevices, you may have to use your finger to smooth out the caulk. Caulk contracts and shrinks, so apply a second layer once it's dried.
Hello, I have a sad situation to share -- a friend of mine who is a very good painter, experienced too, fell off a tall ladder that did not have "boots" on it. (I've never seen those.) Anyway, do you think he should have asked for boots before painting? Possibly it was a situation where he was shy to ask because he wanted the job... (I don't know all the details.)
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.
O'Neil patches shallow holes and divots with Ready Patch because it dries fast, sands smooth, and stays flexible. Deep cracks and rotten spots are best repaired with two-step epoxies, such as those made by Advanced Repair Technology. (For a step-by-step instructions, see Repairing Rot with Epoxy.) The days of using polyester auto-body fillers on wood are over. "They cure too hard," says Portland, Oregon–based painting contractor Kathleen George. "They look good at first, but then they peel away."
I used to work at Sherwin Williams. The best thing to do is specify that you will purchase your own paint. If the painter objects strenuously, he was plaanning on making money in the ways this article outlines. You might pay a few dollars more for paint, but you will have control of the quality of what goes on your walls. Never skimp on paint quality.

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