I paint a few houses every year. I'll be starting a new one next week. I have three different sprayers, and they are great for certain tasks, but I rarely use them for painting houses.
Most of the work that I do when painting a house is prep work. That's usually about 3/4 of my time on the job.
Since you didn't say that you were painting anything made of wood, that will save a lot of time.
My favorite caulk is Big Stretch by Sashco. I think Sashco is the best brand out there and it's worth the time to go to Lowes to get it. I have a Home Depot close by, but they don't sell Sashco products, so I go to Lowes to get it.
Never pressure wash a house!!! There isn't anything worse that you can do to a house then force water into it where it was never built to keep water out. And once that water gets behind your siding, it will remain there for months. The TV Show, This Old House, had a great episode on this where they pressure washed a house, then came back six months later to tear off the siding and see what was going on. They found black mold under the siding, and they even found were it was still wet in areas!!!! Your house is engineered to withstand 60mph winds, not 2,000 psi of water pressure. The pressure washer will blow off caulking, force water into cracks and openings that you cannot see and even damage your siding.
If it's dirty, wash it with a hose and a scrub brush. Add some bleach or a house cleaning product if it's really bad. Most of the time, I sand off the dirty areas in my prep work.
It's almost impossible to get total coverage on Hardie with a sprayer. You have to spray it multiple times, or finish with a brush. I've found that it's faster to just paint it with a brush. The area that the sprayer misses the most is the under edge of the lap siding. But you'll find that after spraying, and going back to look at the Hardie, you'll see all sorts of spots that looked like they were painted when you sprayed, but there's no paint there when it dries. Hardie has so much texture to it that the sprayer just sort of blows the paint over those low areas.
If you are working higher than 8 feet and you need an extension ladder, be sure to have a stabalizer on your ladder. It makes it night and day easier to paint, or work on anything. I also have attachments on my ladder to hold the paint can, so my arms are free to paint and hold onto the ladder.
If you are just on a step ladder, and not painting up very high, be sure to have the bucket that can hold a can of paint on the ladder. I have two of these that I keep on different ladders.
For brushes, I prefer a soft bristle angle brush. They allow me to put more paint on the wall and get thicker coverage. When I'm done for the day, I wrap the brush in a plastic sack real tight to keep air out and use it again the next day. I can go all month without washing the same brush. On some jobs, I'll be painting a couple different colors, so I use different colored sacks for each brush. Home Depot for brown for one, Lowes grey for another and Sherwin Williams white for another. It's nice that each store uses a different colored sack when buying stuff from them!!!
