I have been a professional house painting contractor since 1970. The most difficult project I've encountered is painting exterior eaves and overhangs. These areas are favorite nesting places for stinging insects, including wasps, hornets, and bees. The safest and easiest way to get rid of these dangerous pests is to hire a professional exterminator. I always did my own extermination, but I'll leave that up to you. Once pests are accounted for, we can begin painting.
The first step in painting eaves and overhangs takes place at ground level. All bushes and shrubs need to be cut back as far as possible to make it easy to place your ladders.
Next, choose your ladder. You will need a 16, 28 or 32-foot ladder. Make sure it's long enough to place at a safe angle to the building and not tip over backwards. Have a helper at the bottom of the ladder to hold it and keep it steady.
Determine what type of paint is on the house. To do this, wet a rag with denatured alcohol and rub the paint. If some comes off, it's latex, if not, it's oil based. You must use the same type of paint to re-coat. Otherwise, the paint will come off in flakes and sheets.
You must determine if there is any lead-based paint. There are test kits for this. If your home was built before 1979, lead-based paint was most likely used. To work on homes with lead-based paint, you need to wear a respirator and special clothing. All scraping and sanding residue has to be collected in plastic sheeting, which needs to be carefully rolled up and disposed of in a hazardous waste dump.
Safety is of primary importance while painting eaves and overhangs. You can safely extend your reach by placing one leg at a 90-degree angle to the ladder. You can also extend your reach by clamping a paintbrush on the end of a 2 to 4-foot extension pole. The biggest danger is having the ladder fall off the building with you on it. Be particularly careful at the corners of the building, where the ladder can slide off into thin air with you on it, producing horrible results and a lot of physical pain.
Use common good painting procedures while painting. Scrape off all loose and flaking paint with a triangle scraper, and then sand with coarse (80 grit) sandpaper, followed by fine (120 grit) sandpaper, but don't get particularly meticulous on this. Remember, "High work is not eye work."
Paint going from the outside, inward. Most eaves and overhangs have strut supports. You will find that when you paint them, you also can paint half of the overhang.