The shapes, proportion and scale of the house in the photo are very challenging. The house is symmetrical, but the gable in the center does not have the same shape, pitch or fascia detail. The proportions of the house make adding a porch form (roof) challenging, as PPF suggests. Finally the scale of the porch and any columns should be sympathetic to the rest of the house. The columns in the first photo are much too small, while those in the second and third photos are much to bulky. A very careful study is need to see if and how a sympathetic porch may be added. If it was my house, I might be looking at a horizontal arbor or trellis type porch with appropriate detailed and scaled columns, rather than any sort of pitched roof. Google porch trellis or arbor for ideas. Good luck on your project.

I'd paint it a beige or at least a warmer white. Maybe pick a color from one of the bricks, that way it will blend in with the exterior more.

You can use a pump sprayer with an extension wand. You should be able to easily reach it with a ladder.

Hi Folks - thank you for all of the great ideas. I always knew that step was undersized (we built the house 20 yrs ago and money was tight) but had somehow not Given it a second thought. I can totally see how it would transform the entrance to widen it and build a more gracious walkway. As to can see, we need much more than a paint job. We need an entire new landscape design. a couple of specific responses + yes those brackets are there to hold large, abundant hanging baskets which I usually purchase around Mother’s Day. They do give the front some interest in the summer. yes those “grey things” are planters, which I plant with greenery in the summer. I should have moved them after i Removed everything last fall but I was in a pandemic funk and didn’t get around to it. *shrug* I do plan to replace the coach lights when we paint with something more lantern-like. the house numbers are on the mailbox, which will also be painted. the columns are indeed just lumber nailed together to form a very crude style. No dimensional pieces with architectural flair - just boards. Good suggestion to see what’s underneath. Might be a quick fix to re-skin them. as for the Cracker Barrel color scheme - this made me laugh out loud. Glad I didn't know before now this is the association one makes when one sees our house. At least it will only haunt me until the painters come in a month or so. It’ll be a much more neutral palette with taupe grey, snowbound white trim and probably a navy door. Still working on that. thanks for the Izzy love. She’s a sweetheart. She’s a Coton de Tulear - which is in the Bichon family. Best dogs ever! thanks for your help. Definitely got the ideas flowing...and the budget - much to my husband’s dismay. Cheers to Spring!