Prep - Prep - Prep
Paint surface preparation: The success or failure of any paint project rides at its roots on one basic need: the paint has to stick. It's not surprising then that much of the effort of any paint project goes into making sure this happens. Paint won't stick to a loose or dirty surface. Between air pollution, mold, mildew and the deteriorating effects of the sun, there's a fair amount of work that must be done to get the surface ready to paint.
For exteriors, pressure washing is a great first step to remove old paint and clean dirty or weathered sources. With a combination of high-pressure water and a bleach cleaning solution, you'll knock days off doing the job by hand. If you are working inside, use liquid sandpaper to remove oil, dirt and grime from trim and wash walls down with a TSP (tri-sodium phosphate) solution which is available at most home centers and hardware stores.
Repair surfaces: Now that you can see the wood surface underneath the old paint, you should check for rot, warping and insect damage. Replace any damaged boards around windows and doors, and have your local pest control company inspect any damage you think is insect-related.
Take the time to inspect all surfaces carefully, being alert for anything out of the ordinary. If there is loose, bubbled or peeling paint, it usually means there is a leak and you need to check for a water problem. It's critical to not just ignore these symptoms and paint over them. If the underlying cause is not found and fixed, it will only get worse and your new paint job will not hold up well. This is also a great time to caulk any holes and gaps to improve energy efficiency.