I live in the South where painted brick is very common, and I love it. However, I don't think your brick is ugly at all! Maybe it's the effects of the sun fading it, or whatever, but it actually looks quite nice to me. My concern about painting your brick would be the amount of sun you say your house gets, as it would likely cause your paint to fade unevenly. Also, as someone mentioned previously, painting your brick would just create a different huge block of color to look at, and won't necessarily help to reduce the impression of size. If I were you, I would give my shutters and trim a fresh paint job; Charleston Green shutters and door with a warm white trim would go great with that color brick. Replace the brass door knocker and handle with some something less bright (even antiqued brass would look better). I also like the idea of the planter boxes for the upper windows to add a little softness and to visually break up the facade a bit. You will never achieve a cottage look with your home, as its overall design is inherently more formal, but I think these few smaller changes will go a long way towards helping it feel more cozy and warm and reduce the impression of size. Once you have your house spruced up, deal with the problems of the retaining wall separately. I agree that a painted retaining wall would not look good at all. I like the idea of a stacked stone or similar material.

Black and white photos would look nice around it. Also consider placing the sign off center. Once you start playing with photos of various shapes and sizes it can look much more interesting if your largest piece is not dead center. I recommend using paper templates and temporary adhesive (the gummy type) to plan the wall ahead of time. There are lots of tutorials online about this. I also found that the frames sold by west elm have the most helpful paper templates that come with the actual frame, so it makes the planning easier. Have fun!

I have a gallery wall because I have too much art to display any other way. It is much more eclectic than any of the above inspiration pics, as it includes photos, paintings, wood-block prints, and a wood-burned piece, in a variety of colors and sizes (from 4"x4" to 30"x36"). There are white, wood, black, and gold frames. I laid everything out digitally before hanging, and what I found was that the key was balance. My two white frames are at opposite ends of the display, wood frames are scattered throughout, etc. I tried to balance colors as well, so for example red is scattered throughout. You want to balance the visual weight of things, which can be affected by the composition, color, and the presence of a mat. It's definitely harder to make a gallery wall work when you have a mix of pieces. And I'm sure some people would think my wall is too chaotic, but it pleases me.

everdebz Yes. The bench does have a nook on the other end too, so I could just put pillows on that side and not on this side. Most of the sitting happens on the other end because the dining table sits off center (because its centered to the window which is also off center) and the other end is closer to the table. Usually my main priority is function but on this wall, I definitely want to prioritize what looks better because there are plenty of other places to sit. If the opinion is that I should only just use 1 - black or walnut - then I will do that. Do you think I should I just use one? It seems like black might have the most impact.