Paint the south side when it's most shaded. Latex is almost everyone's first choice for exterior paint because it is easy to apply, cleans up with water, and dries quickly. On top of that, it's long lasting. On stucco it can be applied without a primer and bonds when the surface is damp. For doors, windows, and other places where durability is a concern, pick a glossy paint.
Glossy paint contains more of the resins that give a paint body and hardness.
When painting, try to time your breaks to occur where siding and trim meet or at some other visual transition point. This prevents lap marks and disguises subtle color differences that may occur when you start again. When painting the outside of your house, fold newspaper over the tops of doors and then close them. You won't paint the doors shut. Combine a one pound package of baking soda with a half gallon of water.