I started my young life as a yacht painter in my grandfather's boat shop at 12 and have been painting and house building all my life. We built boats of wood because we had nothing better, we built homes of wood because we had nothing better. I grew up putting wood siding (cedar, redwood) on houses, it was the best we had. Now I tell people use cement siding, paint it once every thirty years if it needs it or not.
Once work begins, hold brief daily meetings to discuss the job and schedule and quash any misunderstandings. If there are surprises, seek middle ground. No contract can anticipate every possibility. Materials may be unavailable. Large chunks of rotten siding may crumble along with the old paint. Exterior jobs may be stopped cold by a week of steady rain. But know that you'll pay extra if you change your mind about a color after the trim is already painted or otherwise add tasks to the project.
I agree with Jeff below, these prices are far below what I see on the market in the Portland Or. area. When one uses the term "paint the house" what exactly does one mean? Any fool can buy an airless paint sprayer and put paint on a house. New homes built with fiber cement siding paint clean and easily but older homes built with wood require much prep work.
Good contracts include descriptions of prep work and repairs; paint specs by brand name, type, color and product number; the number of coats; and a full description of the work, including frequently omitted items such as cabinet interiors and shutters. Minimize delays by specifying that, weather permitting, work will be continuous. Get a payment schedule that minimizes the down payment — the more payment you can withhold until the end, the more leverage you'll have to get the job done well and per your specifications. Insist that contractors provide proof that they carry both general liability and workers' compensation coverage.
As a former professional painter, something that drives me crazy is when I see painters cut in around wall plates. First of all, the amount of time that it takes to cut in is usually much longer than the amount of time that it takes to simply remove the wall plate. Secondly it does not look nearly as clean as it does when the wall plate is removed and thirdly it can invariably leave paint on the wall plate itself which also looks sloppy. Make sure the painter takes them off and then reinstalls them. It's less time.
• One room or the whole house? Applying one coat in one room is a reasonable DIY Saturday project (especially if you have help and beer). Multiply the time spent moving furniture, prepping walls and sanding old trim by the number of rooms in the house, and you might want to hire real help. It's the same outside. You can probably tackle one shady garage wall that needs a little scraping and sanding plus a coat of paint, but covering all surfaces of the house is usually best left to a pro.

WOW! I think the guy I hired read this first and I have photos that would make your skin crawl. Bottom line: he got me for $1900.00. Every single thing he painted had to be completely redone....that's when I discovered he did NOT use the colors I picked, he actually used leftover exterior paint from his mother's house! Because I have pets he said things needed to be sealed first and I did agree to that. What I did NOT agree to was using some kind of foul smelling gray stuff ON MY HARDWOOD FLOORS! THEN he painted them BLACK, telling me that all they were good for was covering over with laminate or carpet. He also dripped and tracked paint all over my ceramic tile floors. PLUS left a wet used paint roller in my garden window and had stuff piled in front so I didn't find it until it had dried. I have no idea how much that is going to cost to repair. Then he left without finishing (thank God) but left the "leftover" paint, uncovered, in the rain. Again, hid it so I didn't immediately find it. Obviously we will be going to court but I doubt if I see a penny from him.
State Contractors  LIC #  388334 , Carry Workers Compensation  Insurance, Liablity Insurance , 36 Years In Painting Business, Over 650 A+ Review in Angie' s List  . We make it a point to never cut corners - keeping you informed throughout the entire project, we are dedicated to understanding and meeting your specific needs for each job. With over 30 years of experience, we are experts at every stage of the process -- from choosing the right paints to the finishing touches.

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