In Mark Twain's classic "The Adventures of Tom Sawyer," Tom tricks his friends into painting his aunt's fence. You probably won't get that lucky, but there are good reasons many homeowners keep their painting in-house. No building codes apply to interior decoration; if you do something dumb, you don't risk life and property as you would if you were, say, tackling a rewiring job; and because labor typically accounts for 80 to 85 percent of the price of a paint job, you'll save a ton by doing the work yourself.
Professional painters have done this before. It’s how they make their living. Through experience, they have learned tricks of the trade and the techniques used to get quality results. They are familiar with the type of paint to use in each situation, know what quality paint is right for each task and know how to achieve a perfectly straight edge – with or without the use of painter’s tape.
The best time to tackle windows is in the beginning of the day, when you're fresh," says Doherty. "But it still takes me an hour to do a standard window." For double-hungs, begin by raising the inner sash and lowering the outer sash until their positions are almost reversed. Paint the lower half of the outer sash first, then the entire inner sash. Once the lower sash is dry, return both to their normal position, but leave them slightly open. Finish painting the outer sash. "Windows take too long to tape," says Doherty. When painting, overlap the glass by 1/16 inch to seal the wood.
Once work begins, hold brief daily meetings to discuss the job and schedule and quash any misunderstandings. If there are surprises, seek middle ground. No contract can anticipate every possibility. Materials may be unavailable. Large chunks of rotten siding may crumble along with the old paint. Exterior jobs may be stopped cold by a week of steady rain. But know that you'll pay extra if you change your mind about a color after the trim is already painted or otherwise add tasks to the project.
Even if you go it alone, specialize to keep your initial investment low. If you do only interior painting, for example, you might get by with one ladder, a few brushes, rollers, basic hand tools and such, for an investment of less than $300. Again, you can add to your tools as you need to (every job is a bit different), and parlay profits into the equipment necessary for exterior painting or working on large commercial properties.