Plan the schedule. Get a grip on the time it will take to bring the project to fruition. Plan for time to move furniture, wall prep, cut in, the painting itself, eating and breaks, and don't forget cleanup and bringing furniture back in. As you plan, err on the side of prudence. Unforeseen events will slow you down, so allow time for these. Remember, this is a multi-day project. Don't try to fit too much into a day. If you move faster than planned, great!
Whether you decide to do the preparation work yourself or have a professional do it as part of your project, proper preparation makes all the difference in creating a smooth and lasting finish. Do it correctly the first time or you’ll quickly end up spending more to fix peeling and chipping paint. Follow this process before starting on your home's exterior. Keep in mind that the process may vary based on your siding materials:
Painters will agree that you should always aim to paint in the part of the year when it’s least likely to rain, has low humidity, and when the temperatures are above 50 F. Rain can wash wet latex paint off a wall, and temps that are too low can affect the way the paint sticks to the walls. Some painters will add additives to the paint if working in very high temperatures to slow down the drying time.

Another type of paint is on the market that claims to be a primer and paint in one. Basically, it’s just thicker paint and costs twice as much as regular paint. Most professional painters aren’t fans, but if you have exterior walls in excellent condition already, and the self-priming paint is the same color as the original paint color, it could certainly save painting time with one coat going on instead of two.
Stripping – $54–$151/100 sq. ft.. “The principle of paint strippers is penetration of the paint film by the molecules of the active ingredient, causing its swelling; this volume increase causes internal strains, which, together with the weakening of the layer's adhesion to the underlying surface, leads to separation of the layer of the paint from the substrate.”— Wikipedia. All the stripper will do is soften the paint. You’ll still have to scrub or scrape it off.

It is helpful then to outline your wall with 2 or 3 inches of primer around the edges and frames before priming entirely the wall. Such a technique should help create a professional look by eliminating drips and splatters. A handheld brush is the best choice for this. For the actual primer application, roller paint can provide extra convenience. Spread the primer pain in V or W-shaped strokes. Once the primer has dried, sand down the bumps and wipe the walls down with a damp sponge.

Prep the house. Wash the walls, remove wallpaper, patch, spackle, seal stains, dry and sand before you attempt to paint. Now is also the time to apply painters tape for trimming, lay drop cloths, etc. Remove all outlet and light switch face plates, collecting screws in a zip-top bag (good opportunity to wash the face plates all at once as well).[4] You can also buy your paint at this time. Don't wait until the last minute. It can take hours to mix many gallons of all your colors. Remember that traffic triples at your home-supply and hardware stores on weekends. Buy on a weekday if possible.
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.
Paint acts as a protectant on wooden siding, slowing down the rotting process. This makes it incredibly important to fully coat the undersides of corner boards on the exterior of your home. Whether you’re undertaking a DIY house painting endeavor or have hired professionals, you should check corner boards and shutters to make sure they’re fully painted.
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.
It’ll cost anywhere from $200 to $6,000 to hire a painter. Expect small jobs, like kitchen cabinets or trim, to run $200 to $2,000. Larger projects, like your home’s exterior, range from $1,000 to $6,000. To estimate your needs, figure paying $2 to $6 per square foot or $20 to $50 per hour. Actual costs vary considerably depending on coverage area, type of work and regional cost of living differences.
Power washing – $0.42–$1.40/sq. ft.. You might think you can save some money by power washing the exterior yourself, but homeowners can get a bit trigger-happy with a power washer in their hands. The pressure from the washer can take them unawares, breaking windows, leaking water into window frames and siding joints, and gouging wood. It’s probably wiser to use a hose and scrubbing brush. Rinse off any cleaning solutions thoroughly.

Prepping a house costs anywhere from $0.50 to $2.50 per square foot. This is almost always included in the total project price. However, the DIYer might negotiate some discounts for completing this work on their own. Be warned, proper prep is key to the quality and durability of the finish. If you do this work yourself, the contractor might no guarantee to finished product.
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