Vinyl siding is one of the more inexpensive siding materials to have repainted, especially with recent innovations in painting materials. Homeowners will first need to vinyl cleaned and repaired, and any clapboards or vinyl sections that have blown off because of climate conditions will need to be replaced. Painting professionals will apply paint quickly and easily over the vinyl siding, much like an interior paint job. The finish, however, may require extensive work and regular maintenance. Expect to pay between $600 (~250 sq. ft.) and $2,000 (~1,000 sq. ft.), with prices likely increasing for the finish. Changing the finish on your siding is not recommended unless it's completely degraded and worn away by the weather conditions.
Generally speaking, based on either personal experience or simply what you have heard, do painters have an outstanding reputation? Rightfully so – answering honestly and without elaborating, most homeowners, builders and property managers would likely say no. As a consumer that is familiar with some painter’s reputation – if you overlooked the importance of conducting extensive research by not asking qualifying questions and getting the proof – what would you say your chances are of having a bad experience? Obviously, pretty likely! Right?
Ideally, you want as much paint on the brush as you can control without making drips or blobs. To do this, Doherty dips his brush about 1 1/2 inches into the paint, then taps (not wipes) each side of the brush against the side of the can. Tapping knocks off the drips and forces the paint into the bristles. "The brush releases the paint just like a fountain pen," he says. Weeks agrees, saying, "Just be sure to keep your brush moving, or it'll start to drip." For more delicate work, such as when you're painting trim or window sash, you'll want less paint on the brush. Doherty again dips and taps his brush, but this time he also scrapes the sides against his can. "The outside bristles are drier and easier to manage," he says, "but there's still plenty of paint on the brush."

This article with comments was terrific - it was so informative. I found the advice useful. It addressed specifics like the condition of the dry wall surfaces, any additional repairs such. pin holes, chalking, smoothing of wall surfaces, absorption of paint and number of coats that may be needed. It should also include insurance coverage, and reflect the clean-up afterwards. Having a written contract with the company's letterhead is a must.

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.
I am in northern Nevada and you have not yet gotten sufficient responses to provide a painting cost chart showing the averages.  I do have a quote from an outside (Not Homeadvisor referral) painter who is local for $2,750 for soffits, patio cover and posts, Garage facia (redwood clapboard above (~300 ? Sq. Ft.) on a 2046 Sq. Ft. home where the walls are 9 ft tall and it is fully stuccoed with plastic stucco surfaces, so not being painted.  

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