Reuse Hole In Brick Which Has Been Caulked

I'm going to be installing a new auto wind hose reel in my backyard and there are a bunch of existing holes in the brick where I plan to install it. Those holes have been filled with caulking. If I drill over into those holes with a drill bit to remove the caulking, will they still be usable for the hole reel installation?

Obviously, I'll ensure the hole is the right diameter for the plugs/anchors but just wondering what the process of removing the old caulking would be and whether I'm better to just use new holes. This area of my house has quite a few holes from previous owners who probably had installed a variety of things on that wall. I'm trying to avoid making a whole bunch of new holes as well if I don't have to.