If there is any peeling — and there usually is somewhere — it's essential to scrape off any loose paint. This doesn't just mean the parts that are already separated from the wood and ready to fall off on their own. Each spot where paint has peeled loose needs to be scraped thoroughly until you can no longer get the sharp corner of a putty knife under any of the surrounding edges of paint. Then, the bare spot needs to be sanded until the paint edges are smooth.
I am a painting contractor and have been since 2001. Make sure the estimate provides in writing: What is EXCLUDED as well as INCLUDED. It should state the manufacturer and type of paint going to be used. Estimate says ALL LABOR AND MATERIALS. My estimates to my customers say "guaranteed coverage" eliminates the conversations of 1 coat vs 2 coat. I have my customers submit colors 5 days prior to start date. Customers need to inform me if they are going to use pure white, dark reds, oranges, and bright yellows they need to inform me in that 5 day window, so I can adjust my pricing for 3 coats. Although this more uncommon now than years past because a lot of paint manufacturers have primer with paint products. Let the contractor know if your doing accent walls. This takes longer to cut in straight lines and it requires the contractor to purchase more paint. If you add anything on the scope of work have the painter write out the description and cost prior to them doing the work. Have the estimate say how many days it will take to perform the work. Ask how many workers will be doing the job. Make sure to enforce that number of workers their everyday until the job is complete. Do not give final payment until you do a final walk through. Walk the job when its almost complete and point out areas that you want fixed prior to the contractors final walk through. Its best to do while the workers are still in that particular area as they will have tarps down and areas covered and it will be easier for them to take care of. Purchase a roll of blue tape and stick it to areas that you want fixed. This is called a punch list.
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Thanks, all, for your time & efforts adding to the article & comments, especially Dave urging requesting both General Liability AND Worker Compensation insurance certificates to protect from real & fraudulent liability--from my experience especially in California, where insurance fraud is a popular income thief, even causing car collisions to collect.
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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.