The last big decision is how to apply the paint. Most pros use paint sprayers because they're fast, but in inexperienced hands a high-powered sprayer can leave drips, thin coats, and a mist that may land on many things other than your siding. If you do hire a painter who uses a sprayer, make sure he is meticulous about removing, covering, or masking off everything in the area that might get hit with overspray: gutters, roofs, windows, shrubbery, walkways, cars—you name it.
Familiarize yourself with construction codes and regulations. All cities have laws that dictate things like how contractors can do business, what types of materials and equipment are okay to use and how professional contracts should be handled. It will be necessary for you to have a working knowledge of these regulations as a private contractor. You can study them on your own time while you’re finishing an apprenticeship or receiving on-the-job training.[9]
When the primer is dry, caulk all small joints (less than ¼-inch-wide) in the siding and trim. Most pros use siliconized acrylics—paint won't stick to straight silicones—but Guertin and O'Neil like the new, more expensive urethane acrylics for their greater flexibility and longevity. O'Neil stresses that it's shortsighted to skimp on caulk. "If the joint fails, you're back to square one." Guertin uses the lifetime rating as his quality guide. "I don't expect 35-year caulk will last 35 years, but it should last longer than a 15-year caulk."
WOW! I think the guy I hired read this first and I have photos that would make your skin crawl. Bottom line: he got me for $1900.00. Every single thing he painted had to be completely redone....that's when I discovered he did NOT use the colors I picked, he actually used leftover exterior paint from his mother's house! Because I have pets he said things needed to be sealed first and I did agree to that. What I did NOT agree to was using some kind of foul smelling gray stuff ON MY HARDWOOD FLOORS! THEN he painted them BLACK, telling me that all they were good for was covering over with laminate or carpet. He also dripped and tracked paint all over my ceramic tile floors. PLUS left a wet used paint roller in my garden window and had stuff piled in front so I didn't find it until it had dried. I have no idea how much that is going to cost to repair. Then he left without finishing (thank God) but left the "leftover" paint, uncovered, in the rain. Again, hid it so I didn't immediately find it. Obviously we will be going to court but I doubt if I see a penny from him.

You can save a bundle by doing the labor yourself. The biggest DIY expense is paint. Other expenses include buying or renting supplies and equipment, like caulk, primer, brushes, rollers, tarps and ladders or scaffolding. Freeman advises applying paint with brushes, not a sprayer. “If you overspray all the window frames and overspray your shingles and your sidewalks and the brick on the front of the house, you do damage that is not easily fixed,” he says. 

I used to work at Sherwin Williams. The best thing to do is specify that you will purchase your own paint. If the painter objects strenuously, he was plaanning on making money in the ways this article outlines. You might pay a few dollars more for paint, but you will have control of the quality of what goes on your walls. Never skimp on paint quality.
All Handy residential house painters are vetted and verified. They’ll also come with their own tools and equipment, so when they arrive at your home, they're ready to get to work. Handy offers friendly customer service, available to connect you with house painting services, whenever you need them. Book your painting contractors to arrive at the time that suits you best and rest assured that they'll take care of every aspect of the job. Your house painting job is backed by the Handy Happiness Guarantee because your satisfaction is important to us.
Sorry it is difficult to trust almost anyone in the trades. It is easier to do the work myself and not deal with strangers in and around my house. When I have to hire someone I tell them up front that I'll be checking every detail, pay extra to purchase the materials myself, and if they don't want the job - well good! I always fine someone who will work with me as I pay a bonus for that.
Buying a can of premium paint, then bait and switch over to low-line products? Again, complete nonsense. Think about it for a moment; the Painter needs 5 gallons of wall finish. So, he buys one can of premium and the rest 'cheap'? How is he going to hide the 4 other gallons? What's he going to hide it in??? He only has ONE gallon of premium. It's not as though he's going to keep older can labels, they would be covered in paint of a different colour.
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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