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.
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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Not all people live where they can hire a painting contractor, like you describe. People who live in small towns can only hire painters who have a very small business, and do two or three paint jobs per week. In this case, you do have to be very careful, when you hire a painter, as we have several, in our area, who are out to make a fast buck anyway they can.
O'Neil patches shallow holes and divots with Ready Patch because it dries fast, sands smooth, and stays flexible. Deep cracks and rotten spots are best repaired with two-step epoxies, such as those made by Advanced Repair Technology. (For a step-by-step instructions, see Repairing Rot with Epoxy.) The days of using polyester auto-body fillers on wood are over. "They cure too hard," says Portland, Oregon–based painting contractor Kathleen George. "They look good at first, but then they peel away."