I assume it is the red you want to paint, I like grayed / greens with red brick and in the trees it has a soothing feel. As for DIY if you have never painted before it is a daunting task especially exteriors. The areas need to be clean scraped and sanded if the old paint is chipping. You need to know what that paint was in order to repaint, you need to be good on a ladder because you will be up there a lot. It certainly can be done just be prepared for a long time to prep before starting.

Do you own scaffolding and have your life insurance paid up?

I like the idea of grayed/greens any idea on the colour choice. Yes, the red has to go,we plan on staining the house. My boyfriend isn't afraid of highest he has a construction background.