Here is where this affects you as a consumer. You select a painter with a contract that says 2 coats, $500 down. You give the company the deposit and pick your colors a couple of days before the project starts. The painter goes to the store with your colors and figures out they are deep base. He (or she) not only needs to charge you more for the paint, but he also needs to charge you for a dark gray primer coat. Ninety nine percent of the time that primer coat is going to be really, really expensive since you already gave a deposit.
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If less than half the old paint is left, however, it may be worth stripping it all off. Guertin gets rid of stubborn remnants using shrouded grinders (like the PaintShaver), infrared paint strippers (such as the Speedheater), or chemical strippers (like Multi-Strip), then smooths the wood with a course or two of sanding. When siding (or bank accounts) can't take the shock of a total strip job, Rich O'Neil, of Masterwork Painting in Bedford, Massachusetts, has successfully hidden rough, well-adhered paint under Peel Bond, a thick primer.
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When the primer is dry, caulk all small joints (less than ¼-inch-wide) in the siding and trim. Most pros use siliconized acrylics—paint won't stick to straight silicones—but Guertin and O'Neil like the new, more expensive urethane acrylics for their greater flexibility and longevity. O'Neil stresses that it's shortsighted to skimp on caulk. "If the joint fails, you're back to square one." Guertin uses the lifetime rating as his quality guide. "I don't expect 35-year caulk will last 35 years, but it should last longer than a 15-year caulk."
This is an area that interior painters can easily cut short to save time. Most contracts don't state the extent of the wall repairs included, so it's up to the painter's discretion how much they will do. If it seems like too much work, they'll usually point out the repairs but don't include it in the bid. They'll then ask you if you'd like it fixed after they start your project and let you know how much more it will cost.