Hi Jim and Welcome to the Forum:
Tom in Kentucky and I painted my house with an airless rig a few years ago. Well, he did the spraying and I was his helper. An airless sprayer on a calm day is no problem but you could buy some thin plastic drop cloths to put over the nearest cars.
Mine is a 1500 sf house and he sprayed it in one day. It nearly worked my butt off trying to keep ahead of him but I was glad to get it done. We cut newspaper pages to fit the panes of glass in the windows, soak it in water 30 seconds or so and put it on the windowpane. It stays in place pretty well unless you blast right at the edge of the paper. Then, when he had painted on past that window, I would pull the paper off leaving a clean window; no paint to scrape off. There are other places, like near the roof or a floor you don't want painted, you can keep a 2' X 4' piece of corrugated cardboard to serve as a shield; just slide it along with the spray gun.