Take photos and measurements of the house to your local equipment rental place. Ask their advice on how to access all the areas that need paint. Also, take measurements of all the areas around the house so you can figure out what equipment will fit based on the amount of clearance.
I did this 2 years ago when I wanted to paint my house. I also thought I'd need scaffolding. However, the rental place recommended a lift instead. That thing was the bomb for accessing my setback 2nd story and massive gables. No setup, just carefully drive it to the side of the house you want to access, load your paint and tools in the bucket and lift yourself up. Easy peasy. The drawback is that it needs a fair bit of clearance around the house since the bigger the lift, the bigger the base.