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We had several neighbors who used to pain one side of their home each summer. Some had to rent a scaffolding system when it came time to paint the side of the house that was on a slope, or to reach an upper story.
I had one neighbor who gradually "lightened" the paint on his house, and no one even noticed, b/c he only took it one shade lighter the first go round. After 4 more years, he had it taken it one more shade lighter. So over 8 years he lightened up the "brown" 2 shades. He did the back, 2 sides, and the front last.
I paint for a living, if you are going to do this off a ladder, use a ladder rated for your weight. If you have siding go across
from left to right and paint as many feet in height as you can reach that you can keep a wet edge, that will give you less brush
marks,like stop and go marks, stay on the side of the house that is the coolest,also think about starting early in the morning
when it is still cool. Your legs will get a real workout being on a ladder all day. Good Luck