Yes the pillars are structural I am not sure if they are all needed but that will be determined by a pro. As for colors A nice shade of gray/ green with that roof and brick will be nice I would remove the shutters since most of them are too small anyway.Your gutters need to be the same color as the roof they are not a design element.Maybe just wood cladding for the pillars painted the same as the trim in the green some nice big planters by the door with seasonal plantings and then decide on a door color

If the columns are hollow make sure there is a gap for air-flow at the top and bottom of the column for air circulation, or they will rot from inside out. As painting goes, see what primers available for this type of weather, if none... nothing will happen being exposed for 1 winter, just keep the snow from piling around them and they should be OK.

Reminds me of all the chase scenes across the rooftops of buildings in any cops and robbers show.

Connections Puzzle #142 🟩🟩🟩🟩 🟨🟨🟨🟦 🟨🟨🟦🟨 🟪🟪🟪🟪 🟦🟦🟦🟨 🟦🟦🟦🟦 🟨🟨🟨🟨 Now look, I could swear I had entered the right combination for yellow, but I guess I didn’t. Never heard of two of the blues, it was a look-up of one of the words that, by chance, led me to a clue of the category.