Prep all surfaces for painting. Power-wash the house first to remove all dirt, then scrape off any cracking or peeling paint. After scraping, sand bare wood and exposed paint edges to improve adhesion. Wash the house again -- this time with a mixture of bleach and water -- to remove areas of mildew.
Cover all nearby bushes and grass with tarps. Remove any debris from around the house.
Paint visible patches of bare wood with water-repellant preservative. This will control the absorption of moisture into the wood -- the primary reason that oil paints crack over time. Wait three days for the newly cleaned house to completely dry. It is important that the house be very dry when the paint is applied because the paint will trap the moisture into the wood once it’s applied.
Check the weather forecast before beginning to paint. You will need dry weather, at the appropriate temperatures. Check the label on the paint can for the appropriate temperatures and necessary drying time.
Paint the house with oil-based primer. Use angle-sash paintbrushes for corners and tight spaces, and paint rollers for larger flat areas.
Paint within two weeks of priming the house or you will need to wash the primer before painting.