Painting your home's exterior is a step-by-step process. First, make sure the surface is clean and dry, and that any problem areas have been sanded smooth. Pick a dry day, and make sure any morning dew has completely evaporated before you begin. Start at the top; then work your way down. For siding, paint the bottom edges first with a brush. Then paint the faces with a brush, roller, or paint pad. When the main part is dry, use a brush to paint the trim. Don't mask off window panes. Instead, overlap the paint onto the glass and scrape it off when it's dry using a razor scraper. This provides an insulating seal between the glass and the sash. Painting or staining shakes and shingles requires a slightly different technique. Start at the top and apply paint or stain to the faces of the top row of shingles. Next, use a brush to do the bottom edges of the row. Work your way down, using the same technique with each successive row. Renting professional spray equipment makes exterior painting a lot faster, but it takes some expertise to apply a smooth, even coat. You might want to practice on an old sheet of plywood or try painting the least visible walls first. If you plan to spray, be sure to cover nearby shrubbery with drop cloths before you begin.
