I am also getting ready to paint the exterior of our home. Ours is similar to yours. I guess that I will just do the ladder thing but scaffolling would be nice. I think you can rent them from Lowes or HD. By the way, what is your choice of color for your exterior?? Good Luck

I was just checking out a loft over at Apartment Therapy and the owner had used a soft green color that could be what you're looking for. I've linked it below. She identified the color as Benjamin Moore's Sienna Laurel. You can click on her House Tour to see more pictures of it. I've personally sampled a color by Glidden, Spring Cactus, that is a soft green, but muted in a good way. I really liked it, especially paired with the darker Safari Green. I've also sampled three other pale greens, Olympic's Lemon Mint and Valspar's Grasshopper and Gleeful. The Lemon Mint color is the greener of the three. Gleeful looked like it would be too intense. And one more suggestion that I haven't personally tried but see a lot of people recommend and that is Ryegrass by Sherwin Williams. Hope that helps. Here is a link that might be useful: loft

my shingles are driftwood - it is not clear in the picture

I've been looking and looking at the photo of the house and I'm not sure it is Craftsman. The third story front gable with replaced windows, the shingles on second floor/clapboard on first floor (the reverse of Craftsman), ...I don't know, but should it be Queen Anne Victorian, would that change suggestions of paint colors?