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Yes, painter’s tape is a great tool when painting trim and walls for a number of reasons. Firstly, it protects the areas you’re not painting. Both brushes and rollers can splatter. Nobody’s hands are perfect, so covering the areas you don’t want paint to get on keeps them clean. Painters tape can also help you get nice sharp lines between paint colors or surfaces, preventing paint from bleeding into other areas. It can also save you time in the long run by reducing the need for touchups. It’s much easier to get clean, even lines the first time when using painter’s tape.

You may be able to paint a high ceiling without a ladder if you have an extension pole that reaches high enough. Some extension poles have telescoping handles, allowing you to adjust the pole's length without needing to swap it out. Another option is to use a scaffold to reach high areas.

You may need to provide your own paint, depending on the agreement you make with the painter. Some painters prefer that you buy the paint and they supply the labor. However, some professional painters get a better price on paint and can pass that savings along to you even after accounting for labor costs.

If you caulk after painting, a few things can happen that you definitely don't want to happen. For one, caulk is messy and can make for an equally messy finish. Second, applying caulk after painting might not provide proper insulation because the paint is underneath the caulk and doesn’t add the same protection as caulk. Third, if you caulk after painting, you'll see the caulk line, which can really detract from the look of your home.