I don't like shingles with brick- personal preference but one is formal one is casual- board and batten or stucco somehow feel more related to brick
Under the windows- remove the siding, add a layer of good 1/2" plywood or hardipanel then use trim to make panels that echo the width of the trim on the windows- lots of ranches have all the window openings in the brick the same size with a couple made smaller with panels. It will be fine.
As to removing the columns and altering the porch roof structure- seems like a way to spend a lot of money for little gain but I guess that is what we all do- you get just as clean in a fiberglass shower from the eighties as you do from a nice glass and tile shower of today...
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