Plan the budget. Costs will vary greatly, depending on price and quality. Choosing mid to upper-grade paint, expect to pay in the area of $350.00 in paint alone for a 2000 sq. ft. house. Add another $100 to $200 in brushes, rollers, pans, tape, and other materials. Don't forget food, if you plan to feed your workforce. When it comes to materials, not all paints are equal. Some truly cover with one coat, some say they do but don't. Your costs will double if you have to apply two coats to everything, so buying the cheaper paint might cost more in the long run. Trust your paint professional salesman (to a certain degree) to tell you which paint to buy. You can generally go cheap on primer, expensive on top coats.
Get estimates from several contractors, request and contact references, search for complaints at the Better Business Bureau[12] and check that the company is properly bonded and insured, as well as licensed in your state[13] . Only pay a small deposit, and don't pay the entire amount until the job is finished to your complete satisfaction (both painting and cleanup).
Prime. Dark colors, stains (once sealed), and previously unpainted surfaces (drywall, spackle, etc.) will need a primer coat, usually white. NOTE: most paint stores & home improvement centers will now tint primer (at no charge) to match fairly close to the color of the finished coat, that way two coats of primer need not be applied.[6] Although not all surfaces need a prime coat, skip this step at your peril! Dark colors will likely show through the first -- or even the first couple-- topcoats of paint. Sealants and unpainted surfaces like spackle patches will absorb or repel moisture in a topcoat at a different level than the areas surrounding them. Applying a good primer coat will help even out these differences. Primer equalizes a wall to a uniform surface. It's like erasing a canvas before drawing a new picture. Although some will argue the point, you generally don't need to spend a great deal on primer or buy special primer. A cheap, 5 gallon (18.9 L) bucket of plain, flat white paint will usually do the trick and cover a large area. Give your primer at least 24 hours to dry (follow its instructions) before applying a topcoat.

Your homeowner’s association might limit you as to how unique you can be with your exterior paint choices. Check with them first to make sure you don’t have to redo your hot-pink-plus-unicorns murals. It can help to drive around your neighborhood to see what your neighbors have chosen and come up with a color scheme that fits in. If you’re not sure, stores can give you small cans of paint so you can paint patches of color in discrete parts of the exterior to see how they look before purchase.

According to Craftsman National Estimator, "High time difficulty factors for surface preparation and painting. Painting takes longer when heights exceed 8' above the floor. Productivity is lower when an application requires a roller pole or wand on a spray gun or when work is done from a ladder or scaffold. When painting above 8', apply the following factors:
Expect to pay between $600 to $3,500 or $1.25 to $3 per square foot to coat vinyl, with prices likely increasing for the finish. It is one of the more inexpensive siding materials to have repainted, especially with recent innovations in materials. Changing the finish on your siding is not recommended unless it's completely degraded and worn away by the weather. You can save nearly half the vinyl siding installation cost of $4 per square foot by painting rather than replacing. Before adding a new coat to vinyl siding,
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