When painting the trim, you don’t have to be neat. Just concentrate on getting a smooth finish on the wood. Don’t worry if the trim paint gets onto the walls. You’ll cover it later when painting the walls. Once the trim is completely painted and dry (at least 24 hours), tape it off (using an “easy release” painter’s tape), then paint the ceiling, then the walls.
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Small random-orbit or pad sanders make this job go faster. (Wallis first covers these boundaries with Synkoloid patching compound so no edge is visible after sanding.) As shown, you want to make sure that there is a feathered, smooth transition from exposed wood to old paint. For areas that might get close scrutiny, you can follow up with a 100- or 120-grit rubdown to erase any scratches.
Specify whether the contractor or you will supply the paint. Check Consumer Reports' paint ratings: In its tests, some relatively inexpensive paints performed better than more expensive paints and cost $10 to $20 less per gallon. But keep in mind that most paints will resist cracking, peeling, mold and mildew. Who does the painting — and how well they do it — is more important than what's in the bucket.

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This was very helpful. I wonder if i would really follow through and check to see if my painter was cheating me. I used a painter I found on Angie's List. This was 5 years ago. He did a great job. I know he did patching only for about a day and a half. We decided on the kind of paint before he started. that is what he used. I don't know if I could stay on top of him and watch him open every can of paint.
Also prime the ends of adjoining boards. This step pays off by slowing the moisture penetration that can lead to peeling at the joints. If the new siding is redwood or cedar, buy a special “stainblocking” primer. Both of these woods contain natural chemicals (tannins) that can bleed through paint, causing brownish stains. A stain-blocking primer will seal in the tannins.

Lastly, chose a sheen to match the needs of the space. Flat finishes hide imperfections well and absorb light which can make the paint look darker. Eggshells and satins are tough enough to be used in family rooms, kids' rooms, and hallways but don’t hide surface imperfection well. Semi-Gloss and high-gloss finishes are primarily used for trim because they accentuate woodwork details and clean up easily.
• One room or the whole house? Applying one coat in one room is a reasonable DIY Saturday project (especially if you have help and beer). Multiply the time spent moving furniture, prepping walls and sanding old trim by the number of rooms in the house, and you might want to hire real help. It's the same outside. You can probably tackle one shady garage wall that needs a little scraping and sanding plus a coat of paint, but covering all surfaces of the house is usually best left to a pro.

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