Painting a two- or three-story home can be challenging if you're not used to working with heights and from ladders. To paint a second-floor exterior, you'll need at least a 24-foot extension ladder. Painting from a ladder or roof is slower work, because you can only do a small section at a time before moving and repositioning the ladder. You also need to be reasonably fit, comfortable with heights and willing to observe ladder safety as if your life depends on it--because it just might.
Assess not only the height of your home, but the ground around your house. If it's not level, you may need to use a ladder leveller, and if there is a lot of landscaping or shrubbery, this can present an accessibility problem. Also be aware of tree branches and power lines because you'll need to take care when working around them.
Purchase, borrow or rent a ladder. If your house is two stories without any peaks or high chimneys that need to be painted, a 24-foot ladder should be tall enough. For peaks and higher areas, you may need a 28-, 32- or even 40-foot extension ladder.
Work from the top down. Painting the second floor first not only gets the harder portion out of the way, but allows you to fix drips and ladder marks lower on the house.
Use a ladder leveller, available at most paint and home stores, for very uneven or sloping surfaces. There are several styles: choose the one you're most comfortable with. Some attach to the ladder legs to compensate for a slope, others are nonskid platforms that support the ladder.
Put your paint in a smaller bucket and keep it no more than half full when painting from a ladder. Consider a bucket hook, which allows you to hang the bucket from the ladder, leaving you both hands free.
Use a 5-gallon bucket and paint roller grid for rolling from a ladder. Hang the bucket from the ladder. This way you won't be climbing up and down the ladder with a drippy paint roller filled from a roller tray.
Buy or rent stabiliser bars so you can work more easily around large windows if you can't reach around them otherwise.
Paint the soffits and siding first. Allow it to dry for at least four hours, and then paint the trim. Tape or tie rags to the top of the ladder to prevent it from scuffing the freshly painted siding, or buy foam wall protectors which slide over the top of the ladder rails to protect the wall.
You will need help moving and setting up a 32- or 40-foot extension ladder unless you're used to doing so and quite strong. Wear sturdy closed-toe shoes or boots when working on ladders.
Read and pay attention to all the warnings and instructions on the ladder label, or check the link below. Ladder accidents are very common but easily avoided by following safety instructions. Never use a damaged ladder. All the parts should be in good working condition, and there should be no bent rails or rungs.