First time repainting the gable and after some advice😢😂:

Gable
Hi everyone, the paint is peeled off due to lack of previous owner's maintenance. Could anyone share what exactly I need to do step by step to repaint it?
If I cut off small smaple from the gable for tinting wont it be risky that I might damage this gable if I chip too much? if its an issue, I actually dont mind painting it with a similar color. So I should show the counter a photo of my gable?
(I have actually enquired a few roofers / painters, But they cant. They cant do it as they regard this as a small job unless substantial price is paid for their time.)
So this is something I will do myself. I am young and fit and I have a mate to look out for me, so I could go to the roof to repaint it myself. But I am clueless as to where to begin with.
Thank you for any advice!