Small random-orbit or pad sanders make this job go faster. (Wallis first covers these boundaries with Synkoloid patching compound so no edge is visible after sanding.) As shown, you want to make sure that there is a feathered, smooth transition from exposed wood to old paint. For areas that might get close scrutiny, you can follow up with a 100- or 120-grit rubdown to erase any scratches.
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When the primer is dry, caulk all small joints (less than ¼-inch-wide) in the siding and trim. Most pros use siliconized acrylics—paint won't stick to straight silicones—but Guertin and O'Neil like the new, more expensive urethane acrylics for their greater flexibility and longevity. O'Neil stresses that it's shortsighted to skimp on caulk. "If the joint fails, you're back to square one." Guertin uses the lifetime rating as his quality guide. "I don't expect 35-year caulk will last 35 years, but it should last longer than a 15-year caulk."