Scale has one of the biggest impacts on deciding whether to hire painting help or take matters into your own hands. If you want to paint your home, consider whether or not this is a realistic task to take on yourself. For instance, is your house multiple stories or a townhouse? Do you just want to paint the kitchen or the entire exterior? Once you factor in the time it takes to do the prep work and lay down multiple coats of paint, a DIY paint job can get complicated. If the house painting job is extensive, you may want to leave it to professionals.

The following guidelines will set you up for success. First, start at the top and work down. Second, paint out of the sun’s glare, since the sun will cause the paint to dry too quickly and flake or blister. To avoid marks, try to brush from one wet surface onto another. If you do have to paint onto a dry surface, overlap the wet paint onto the dry surface by several inches.
Determine the coverage area for each color and estimate the number of gallons you'll need for each. For odd walls with angled ceilings, make your best guess. If you're not comfortable doing this, measure the wall at its highest height and multiply that by its width. Now subtract the lowest height from the highest height, multiply that number by the width, cut that answer in half, and finally subtract that new number from the original height by width. That should give you the wall area.
Carefully consider the gloss level. The shiny gloss paints are easy to clean, but will make any wall blemish stand out. The flat paints will help disguise wall blemishes, but can be difficult to clean. Generally, you'll want glossier paints where there's lots of steam or cooking (baths and kitchens) and in high-traffic areas. Flatter paints are preferred for large walls and ceilings.
If the exterior of your home is unpainted or has been scraped and sanded, you will want to lay down a coat of primer. Make sure that the primer you’re using is right for the surface you’re painting. While most surfaces can be treated with acrylic primer, some surfaces, like cedar and redwood, require oil-based primers. The oil stops the wood tannins from bleeding through the topcoat.
Paint supplies cost anywhere from $10 to $100 or more depending on what you need. Painters will typically provide most of the supplies for a project, but sometimes they will allow you to pay for solely labor if you provide all the materials yourself. You might decide to do a DIY paint job down the road. In which case having these supplies on-hand will save you time and money.
Practicing ladder safety is key. When using an extension ladder, always test that its resting at the right angle by putting your toes against the feet of the ladder and extend your arms outwards. At the proper angle, you should be able to rest your hands on the rung in front of you comfortably. When on a ladder, you should always keep your hands free and maintain a steady center of gravity.
It's up to you. Outside is much harder because it requires more prep, patience, time, help, money and of course, effort. I have been painting my own houses and rental properties interiors for 20 years, and I painted the exterior of one, once. I then had it promptly done again by professionals who said it would have been cheaper if they didn't have to undo my work first. My advice is to get pros for the outside because everyone will see it.
Each type of siding will need to be treated differently when it comes to primer and paint at different price points. Exterior paint costs between $35–$80 per gallon depending on the quality you choose. It’s not always true that the more you pay for your paint, the longer-lasting your paint job will be, but you do need to be careful when researching exterior paints to make sure it can weather the local elements well.

While vinyl siding salespeople claim it never needs to be painted, it does lose its color strength over time, and the degree of fading can vary depending on which sides get the most exposure to sunlight. Perhaps it still hasn’t faded, but you don’t like the color much. You can’t go any darker than its current color, though, because the siding is designed to absorb only so much heat, and a darker color could cause it to buckle. Vinyl paint is available in many colors. Brush painting and roll painting vinyl siding costs $43 per 100 sq. ft., and spray painting costs $34 per 100 sq. ft.
Like the rest of your home’s exterior, you should start from the top down when painting exterior trim. If your window sills look particularly weather-beaten, you might want to give them a second or third coat of paint. When painting doors, paint the panels first, then the rails and stiles, and finally the edges. For more details, read up on trim painting guidelines.

A gallon of paint costs $15 to $40 and covers about 350 square feet with one coat. Designer varieties can run over $100 per gallon. Your contractor pays 50 percent less than what it runs in a home improvement store. You’ll also need to spend another $20 to $100 on supplies like brushes, rollers, masking paper and plastic. A professional will have these items on-hand.
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06/14/17: Renato completed an exterior painting project for our relatively large single family home in Stamford, CT last weekend. Project did not begin well especially with the prep, repair/carpentry work, but then Renato took full control and ensured that the work done was to our satisfaction. The final result is outstanding. Minor damage to window screens, gutters and plants. Ensure that your window screens, gutters, and shutters are numbered and stored indoors or if kept outdoor covered properly against the elements. The project can be extensively delayed due to rain and you may find yourself dealing with insects and/or flooding in basement and dirty/bent/ mismatched screens/gutters/shutters. Overall we had a good team working on our project and we are satisfied with the finished product. The house looks great!
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