Examine the entire surface of your house, looking for problems such as peeling paint, open joints or seams, wet or rotted wood and mildew. You must identify, repair and resolve these problems before you pick up a paintbrush.
Flaking paint occurs when moisture collects under the painted surface. The moisture enters the wood siding from the unpainted side, gets absorbed and then dries. This causes repeated swelling and shrinking of the wood, which makes the paint pull away from the wood surface, leaving it cracked and peeling. Locate sources of moisture by checking the area for leakage from the gutters or eaves of the house. If the flaking paint is near a bathroom or kitchen, the pipes may be sweating or leaking or excess heat may be causing condensation.
You may need to use a ladder to get a close look at some areas. Or consider using binoculars to examine your siding's condition from the ground; either of these will better help you identify potential problems.
Familiarize yourself with basic ladder safety procedures. Be wary of bee and wasp nests, especially when you are on a ladder.
Be very careful around overhead electrical wires, especially when moving ladders around or painting near where service lines attach to the house.
Follow directions and heed safety warnings on paints, chemicals and cleaners.