Is the sun on the front of the house a problem? I can see wanting a small portico or entry awning, but it's amazing how sleepy the house looked before and how awake it looks now. Regarding painted brick, I grew up in a house with white painted brick and no one ever complained about intolerable maintenance. The more unified front aspect could be a strong positive.

You've got shakes and brick on the front and, what appears to be, vinyl along the side. Was the house built like this in the 1980's? If so, then just paint it all one color. Or remove the front brick and shingle and re-side. Or just re-side the whole thing in fiberboard if your budget allows. If you want to play with the roofline, then that's going to require some input from a professional (like an architect). I think painting it all one color is the answer. However, I am reading a book on Bungalows and Craftsman homes and they painted the upper and lower floors different colors specifically to make the homes appear lower and wider. So maybe that's an option--but you don't have a visual divider between the 2 floors on the sides so, again, I would just go with all one color. You don't need to make it look less like a dutch colonial, you just need it to look like the prettiest Dutch Colonial. You need nice landscaping.

I like your new door. You have a range of colors you could paint it. Is your house all siding or brick? Are the window frames wood that could be painted? I would take down the shutters. Some of the windows are just wrong plus the shutters are so pale you can hardly see them.

I recommend that you check out what you can do to reveal the brickwork and stonework around your windows and setbacks. I don't know what can be scraped off, but I don't think ornamental shutters will look good on top of them. A fiberglass fabricator could probably embellish the columns in several ways, including providing squared off caps and footings Actually moving them needs to be checked out carefully for structure support, which I presume you know. I still don't favor moving the columns to create a wide opening. In the part of the world where I live (New England) a wide columned portico is almost an iconic logo for a senior living facility, as directional as the MacDonald's arch If it isn't so where you live, don't worry about it. I quite like the idea of creating a balcony, and for that money, I'd make it so I could use it, with double doors leading out to it and safe support underneath. (I think I'd skip the ground level railings and maybe increase the size of the oval window.) But it would be a good investment I think.