I really dislike painted brick and yours is so neutral I think going a shade darker than the darkest color in the brick would be good for the siding, You might think about matching the garage door to the front door if going wood This is one of my favorite ideas for landscaping a MCM ranch I have a MCM ranch and am going to work toward this idea for my landscaping

The house itself is asymmetrical, both stories. I think you need a professional to design a new roofline for the porch, and this is where the bulk of your money will go. Your two inspiration pictures are of White House’s with black framed windows. Forget shutters, they need to go. Paint the house a nice, creamy shade of white. Whatever color you choose, paint the garage doors the same unless you are replacing them with more modern looking doors. I would go ahead and paint the window frames charcoal. You will need a charcoal roof when it’s time to reshingle. Cut down the shrubs. That front porch area is what is really defining the house, and once you redesign that area, the rest of the house will flow from there.

That's a wonderful first home and looks well maintained - congratulations. From the examples you've been given, I would go with one of the darker greens, or darker brown. My own single story MCM is dark unsweetened chocolate brown - all of it, no brick other than built in planters in front - and in searching back through neighborhood photos, has been this color since built 1955. I have no plans to change it. I like the way it blends into the landscape as though a part of it, and not something just dropped into place from somewhere else ;0) I think blue would have that effect on your home with the treed background. One thing the PO had done here was paint the underside of the soffits warm white. I think if the darker color, it would appear a little dark when inside looking out...you might want to keep that in mind when painting along your parking and basketball hoop area and keep the part the overhangs the brick light colored on the underside. No one will notice from outdoors.

If you scrape off a bit of the window trim, what are the paint colors underneath? As for the wood siding that has darkened with time, consult a local paint company to see what they recommend for renewing the stain or painting over it. There are areas you can brighten up without painting the siding. For example, you can paint the windows and their trim and the underside of the soffit in light beige, sage green, red brick colors. Put some masking tape up around the windows to see if you like beige.