Paint sprayers FTW!
I’ve owned a Graco sprayer for almost 20 years, and borrowed my father-in-law’s long before I bought one. It’s the wheeled cart kind that I can park over a 5 gallon pail. It’s incredible for painting the house, fence, deck, and everything else outdoors. I can literally paint the house almost as fast as I can climb up and down the ladder.
Prep is critical. I have to tape the windows, doors, and other openings by covering them entirely in plastic masking film, and sealing the edges so there’s no blowback to leak in. It takes nearly a day to tape.
While painting, I use a dropcloth over the grass, and hold a screet to keep from spraying the shingles and foundation; that saves time and tape.
Before painting, I suit up - goggles, a cotton balaclava, gloves, long sleeves, and a mask. It’s definitely clothing that will overheat you quickly - so getting it done before noon is important. But all that prep pays off. I can paint the whole house and garage (14 gallons) in about 6 hours, and start cleanup by about lunchtime. (Hidden time-suck: cleanup takes hours of flushing and cleaning the hose, gun, and pump. But I do that in the yard under the shaded comfort of a tree.)
As far as I can tell, the handheld sprayers have little utility - as you noted, a quart or litre of paint is gone almost instantly, and it would be maddening as hell stopping every five minutes to refill while trying to paint any area of consequence. And all sprayers are worthless indoors, except for new construction. But those little airless pumps are the bomb when it comes to exterior paint jobs. For less than the cost of hiring a painter one time, I’ve painted my house three times (we re-sided a few years after the first time) and painted other family members’ structures, too.