When the homeowner is at the point of hiring a painter, they generally will have colors selected or at the very least a color in mind. I always ask for the colors before I bid a job. Dark colors, high sheen colors and specialty finishes require more labor, this drives price. If its not a color change or I'm going over a similar color I give the pricing option of one or two coats. The best advise I can give based on 25 years in the business is to put it all in writing,colors, brands of paint preferred, when the work can be done, who moves furniture and how payment will be handled. I never get up front money. BTW you most definitely get what you pay for with paint. Higher quality products results in and better looking job. Don't be a cheapskate when it comes to paint or the painting contractor.
The last big decision is how to apply the paint. Most pros use paint sprayers because they're fast, but in inexperienced hands a high-powered sprayer can leave drips, thin coats, and a mist that may land on many things other than your siding. If you do hire a painter who uses a sprayer, make sure he is meticulous about removing, covering, or masking off everything in the area that might get hit with overspray: gutters, roofs, windows, shrubbery, walkways, cars—you name it.