Choose a calm day, preferably with humidity lower than 80 percent and no rain threatened. Be aware that over-spray can drift up to 20 feet, even on a relatively calm day.
Move patio furniture, toys and even cars into the garage or away from the house. Remove or mask exterior lights, house numerals, awnings and other elements you don't plan to paint.
Buy or borrow a hand masker. This handy tool allows you to apply tape and masking paper or plastic quickly and precisely over windows, masonry or anything else you don't want to dust with over-spray. Mask off everything you need to, and use heavy drop cloths to protect plants adjacent to the house.
Strain your paint into a clean bucket, using a mesh strainer from the paint store or a clean pair of nylons. Refer to the label for thinning directions. Some materials can be thinned with up to a pint of water per gallon for spraying, others should be applied as they come from the can.
Flush the sprayer with clean water if you are using water-based paint, or mineral spirits if using oil-based paint or stain. Make sure you have the correct spray tip for the material you are using--the tip for exterior acrylic latex paint must be a different size to a tip for oil-based stain.
Start spaying on an unobtrusive part of the house. Use a light touch with the sprayer because it's best to paint two thin coats than one heavy one, which can drip or run.
Experiment with the pressure setting. You should be able to apply an even fan of paint from about 2 feet away from the siding. If the fan is uneven or thin, your pressure may be too low. If the gun "kicks back" in your hand and the paint fan is runny or drips, it's probably too high.
Keep the spray gun perpendicular to the surface instead of arcing it. Squeeze the trigger after you start moving your hand, and release it just before you stop. Apply paint in 3 or 4 foot sections, working methodically from top to bottom.
Wait until the paint is dry before removing masking tape, plastic and paper. Before you remove the masking materials, make sure there are no light or missed spots on the siding.
Wrap the entire spray rig and paint bucket with a large plastic bag or plastic sheeting to prevent it from drying out if you're taking a break. At the end of the work day, flush the sprayer with clean water and then run some mineral spirits through it.