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You should generally drill into the mortar joints when installing shutters on brick. Mortar is softer, which makes drilling easier and puts less strain on your tools. It also lowers the risk of cracking a brick—something that’s a lot harder to fix. Mortar holds fasteners well enough for standard shutters, and if you ever need to patch the holes later, it’s a much simpler job than dealing with damaged brick. Just keep in mind that if your mortar joints are too thin or the hardware calls for brick anchoring, you'll need to check the manufacturer’s recommendations and adjust accordingly.

Removing paint from brick can have both aesthetic and practical value. Some people prefer the timeless look of bare brick, making it worthwhile to remove old paint layers. Brick also lasts longer when unpainted, as paint traps moisture, causing the brick to deteriorate more quickly. If your brick walls are already in bad shape, stripping the paint off might do more harm than good.

The exact cost of bricks depends on the type and size of the bricks you use for your project. Generally, standard clay bricks cost between $350 and $850 for a thousand bricks, or an average of $550. Brick veneer costs around the same for materials but is easier to install than solid bricks, so you’ll save on labor by choosing this option.

You can use a regular drill to make pilot holes for gutter brackets in the wooden fascia board around the top of your house, but it’s not the best tool for brick. Instead, you’ll need a heavy-duty power tool like a hammer drill with a carbide tip bit.