We received the painting estimate and I was pleasantly surprised. It's $1700 for the one side of the house, including a pressure wash, scraping, sanding, priming, and two coats of Sherwin-Williams exterior paint. I think we're going to go with it after we check references. While we could certainly do it ourselves for less, I'm not sure the time, effort, and probable broken bones are worth the effort.
We're planning for the end of June for the work so I'll put up some before and afters when it comes to that time.