Pressure-wash the entire surface to be painted. Remove any dirt, mold, grime and loose paint. Let the siding air-dry thoroughly.
Sand the siding with a wood-specific sandpaper until smooth where it has rough edges from wear or weather.
Apply one coat of a first-coat primer to any bare spots. Where the old paint is not loose, leave it on. You don't need to apply primer there.
Caulk around windows, door jambs and nail-holes. Allow it to dry overnight, or at least 12 hours.
Brush on a top coat of paint with your 4-inch brush, which should be about 1-inch thick with tightly packed bristles. If you can see the primer or previous coat of paint through the first coat after you have allowed it to dry according to the manufacturer's specifications, apply a second coat.