If you decide to hire help, have several contractors inspect the job and provide proposals. You'll probably find huge price differences for the same job. A Checkbook undercover shopper got quotes from nine Washington-area contractors to repaint the walls, ceiling and trim for a living room, dining room, family room, bathroom and kitchen. Including paint and supplies, prices ranged from $2,650 or less to more than $6,500.
Paint gets more expensive as you go from flat to gloss. The difference is usually around $1 per gallon per sheen upgrade. Flat is the cheapest, then matte flat or eggshell, satin, semigloss then gloss. Paint also gets much more expensive the darker it gets. A white or neutral paint color can be as much as $20 less expensive than a deep base red or blue.
Color is always the first consideration when painting a home. Most paint manufacturers offer samples to try that can allow you to make a more informed decision. Because light within a room may vary from wall to wall as well as from day to night, try painting a large piece of poster board in the color or colors you are considering. Move the board from wall to wall and look at it for a minimum of 24 hours at a time in each space to make sure you like the color before committing.
When painting the trim, you don’t have to be neat. Just concentrate on getting a smooth finish on the wood. Don’t worry if the trim paint gets onto the walls. You’ll cover it later when painting the walls. Once the trim is completely painted and dry (at least 24 hours), tape it off (using an “easy release” painter’s tape), then paint the ceiling, then the walls.
 I started my young life as a yacht painter in my grandfather's boat shop at 12 and have been painting and house building all my life. We built boats of wood because we had nothing better, we built homes of wood because we had nothing better. I grew up putting wood siding (cedar, redwood) on houses, it was the best we had. Now I tell people use cement siding, paint it once every thirty years if it needs it or not.
Pros prefer 5-gallon buckets with a roller grid to roller pans. They hold more paint than pans and, says Doherty, "It's tougher to tip over a bucket." A bucket also lets you box, or mix, two or three cans of paint to avoid color discrepancies. To use a bucket and grid, dip the roller a quarter of the way into the paint and run it over the ramp to work the paint into the nap.

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