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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.
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.
Sand the trim with a fine-grit sanding sponge. Sponges get into crevices where sandpaper can’t go and let you apply even pressure. Then apply the ﬁrst coat of paint, let it dry at least 24 hours, lightly sand it again for a completely smooth surface, and apply the second coat. After each sanding, vacuum the trim, then wipe it down with a tack cloth to remove the dust.
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.
They painted our home exterior about 12 years ago and did the interior about 9 years ago as part of a major remodel. As it was time to re-paint the exterior again, we used James Lee again, and were very glad we did. In walking around to find 'punch list' corrections after they were done, there was pretty much nothing to find - they did a great job.