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To win work, contractors generally have to bid against other suppliers. To make an accurate bid, they estimate the time and materials required to complete the job. They measure the area to be painted and discuss the type of finish the customer requires. They assess the quality of the surfaces to work out how much remedial work they must carry out before painting. They might have to remove old paint or wall coverings, or repair cracks and other damage. They also calculate the cost of any essential equipment, such as scaffolding for exterior walls.
Ask companies to include all details in writing. Although that sounds simple enough, too many contractors submit offers such as "paint house for $5,000." A friendly contractor may offer a reassuring handshake and promise that the crew will take care of all the details — starting on time, working every day, cleaning up, etc. That's great, but why not include each point in the proposal? If it's a challenge to get a written description of labor, materials and other details, things will probably get worse when the work starts.
Some contractors work on time and material others on a firm contract. I would never hire the former and am leary of the latter. A contractor may low-ball a bid to get the job planning to make a killing on change orders. If you say good morning to them, they charge you extra for that. If the contract is not very, very specific and extensively fleshed out or if they display their change order schedule prominently on top, show them the door.