You can typically complete all of these preparations for an entire house in a single day or over a weekend. If you're painting a porch or an outbuilding, it may only take an hour. If you're painting with latex, you can start the following day; solvent-base paint does not adhere well to moist surfaces so wait several days until all the washed surfaces are absolutely dry before applying this type of paint.
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.
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