There's a porch on both the front and a single story addition on the back where the roofline is highest, so a scissors lift won't work. A cherry picker might work on the front, but we don't have good access in the back.
I'm told the prior owner painted it himself with an extension ladder placed on top of the porch and addition to reach the peaks. Both roofs are slanted. No way.
@lthenderson I've thought about doing everything I can and trying to get a pro to do the stuff I can't reach. My concern is actually finding someone good who would take that sort of job. Seems like there's ample work out there right now, and I'd be worried I'd get stuck with a half painted house and nobody who would be interested in finishing it up.
@GilesMM Owning an old house with a tall, steep roof has made me appreciate the virtues of ramblers. So much easier to do work on the exterior when it's a single story with a low pitch roof.
My now retired partner and I would only build houses with 6/12 pitches or less as we got older because of this!
Scaffolding is not often used for painting because it gets in the way of painting, most painters don't own it, and you don't really need access to every square foot of the siding to paint (pro's use sprayers).
I use pump jacks for siding repairs, but most painters just use a lot of extension ladders for painting, or ladder jacks, which mount to extension ladders and enable you to put a plank between two ladders. These are much less safer than pump jacks because they only have a walking plank, where a pump jack setup has a working plank behind you, making it much harder to fall, and you can go up and down at will with the pump jacks, so you aren't reaching and becoming unstable.
It's actually very difficult to do much "work" from a ladder, especially near the top, as you're too close to the side of the structure.
The best way to put a ladder base on a sloped roof is to install roof jacks and planks first (toe boards): this helps you to not fall off the roof and gives a brace for the ladder feet. Of course, you will likely damage the roof shingles so you also want to set up a piece of plywood that will protect the roof and lock to the roof jacks and not just slide off the roof.
A boom lift is also available from the rental yards and is by far the safest option, though expensive. You want the version with big off road looking tires, although they aren't quite as off road capable as they look. If you're going up 40' you will still get spooked even in the boom lift, but they are pretty fun once you get used to the swaying. Just be careful "driving" them from the boom when extended. The rental yard will deliver and pick up the machine.
A one week rental should give you plenty of time.
