Intro
No matter what kind of siding you have on your house, perform a general inspection before you prepare it for painting. Look for mold, mildew, damaged siding, and wet or dry rot.
Once you've inspected the siding, preparation follows the same general order -- remove mold and mildew, wash away dirt and chalking, repair or replace damaged siding, remove loose paint, and spot-prime the affected area.
To get the best finish on glossy surfaces, scuff sand them using a sanding block, pole sander, or sanding pads and 120- to 150-grit sandpaper. Do not oversand; just scuff the surface lightly to provide a roughened tooth for the new paint.
Water is the chief enemy of both wood and paint, so caulking gaps is important. Apply a top-quality all-acrylic or siliconized acrylic caulk to inside and outside corners, joints, seams, and other gaps where water could penetrate the wood's exterior. These caulks will adhere to a wide range of materials, even when they are wet.