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."
You are right on with this - why do people leave switch plates on when it's just so easy to take them off? Another thing that happened to us - we had the popcorn ceiling taken off and the ceiling painted white. When the job was done and I later went to change out all the fixtures/fans, they had left every fixture in place, so there was a large patch of popcorn and unpainted ceiling left behind - it just didn't dawn on me to specify that they take those down before scraping and painting. It was kind of a mess.
I have a Home Improvement/Painting business, and Angie's List always advertises that that everyone is out to get them. Of course there are people who try to take advantage of homeowners My reputation and repeat business is based on word of mouth. Shoddy work is always a way to get put out of business quick. As far as strictly painting, preparation is a big factor in getting a quality paint job. If you don't prepare the surfaces you are painting you are spinning your wheels, and wasting money, no matter what paint you use. Getting a deposit from a customer is beneficial, but not always necessary. Sometimes it is a godsend, when you get stuck by the customer, which has happened to me more than once
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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.