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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.

Yes, you can enlarge windows in a brick house. Your masonry contractor will need to cut away exterior brick to make space for the larger window, and you may also need to consult a structural engineer to make sure the window is properly supported inside the frame of the house.

Costs depend on material type, labor, chimney requirements, and structural reinforcements.

If your old bricks are in decent condition and you have the space to store them where they’ll be protected from the elements, keeping old bricks is often worthwhile. You’d spend anywhere from $70 to a few hundred dollars to have them removed from your property, in which case you won’t be able to use them for future projects. Holding on to old bricks in good condition means you can use them later for other DIY projects, potentially saving yourself some money on disposal and new materials down the road.