Painting your home's exterior is a major undertaking. However, the benefits outweigh the risks. You'll save thousands of dollars, extend the life of your siding and trim, and raise the value of your home with a small investment in equipment and materials. To paint crisp, straight lines, you'll need a keen eye, a steady hand, and some practice. You'll also need the power and courage to move and put up large ladders, as well as the ability to operate from them once they're in place.