Scrape peeling paint off the exterior of the house with a paint scraper. If you're painting only the trim and fascia boards, use a 24-foot or 32-foot extension ladder to scrape the highest areas of the house first and work your way down. If you're painting siding, trim and fascia, set up two extension ladders and a plank. Hook one ladder jack onto the rungs of both ladders at an equal height. Rest a ladder plank on top of the jacks. The plank allows easy walkable access to a large section of siding.
Sand the exterior trim or siding with 50-grit or 80-grit sandpaper. Reposition the ladders at the top and work your way down to the bottom. Use an orbital electric or battery-powered hand sander for easier sanding. If you're working off a ladder plank, sand the siding as far as you can reach before moving the ladder plank down to a lower level.
Protect the ground beneath the house exterior. Spread canvas drop cloths over the grass, concrete and bushes. If you're not painting the shutters, tape a piece of painters plastic over the top to protect from paint sprinkles. Cover the windows with plastic. If you're painting above a separate lower-level roof, spread drop cloths over the shingles.
Pour one gallon of primer into a clean, empty 5-gallon bucket. Clip a bucket hook onto the handle of the bucket. Stir the primer thoroughly. Hook a 9-inch paint roller and 3-inch paint brush onto the side of the bucket. Drill a screw into the side of the paint brush so you can easily hang it on the side of the bucket while working.
Reposition your extension ladders, or ladder plank, to the highest point of the house and begin priming all surfaces you will paint. Hang the 5-gallon bucket off the ladder rung using the bucket hook. Prime around windows, cracks and crevices using the 3-inch paint brush. Roll the primer over the surface right after using the paint brush. Prime the exterior from top to bottom.
Reposition the ladders again and apply the first coat of exterior paint using the same methods used for priming. Allow the first coat of paint to dry. If necessary, apply a second coat of paint.