Secure funding
Shop for best paint sprayer & paint
Purchase sprayer and paint
Start at the top - I hate ladders and scaffolding
Pressure wash entire surface to be painted
What to do about rotting wood siding

Learn to operate airless paint sprayer

Become familiar with equipment
Read instructions and safety measures.
Secure solvents (mineral spirits for oil, warm soapy water for latex.
Pump lube
Assemble equipment and power cords

Spray

Respirator, safety goggles, and coveralls
Telescoping sprayer gun