I would not paint the brick. The brick is what makes your house stand out and I do not like grays or blues with brick.Do the siding the same as the window trim and you could do the garage door the same . Then go to work with landscaping that will up the MCM look much more than paunting the brick.

We need to remove brick under bay window because it’s falling off, but the rest is ok. We’d like to replace it with something else and paint the red brick to match whatever material we use, possibly charcoal to bring out the dark in roof. Thinking either vinyl stacked stone siding, vertical siding or vinyl shake siding. Also should we do the whole window wall or just under window. I’d love to keep garage door & front door red but give it a fresh coat.

any of the colors mentioned above will work. very similar to yours w/the gabled portico. see how they have it w/a black fascia and bright white elsewhere? can't tell if yours is bright white or creamy white. (and you should redo your house numbers. you can barely see them) tried to photoshop the black here and gave you candy apple red door gave you a vintage looking front door in black, and a diff light. emerald green, light, address placque cobalt yam slate gray what this home needs is landscaping. proper landscaping will take this old colonial to a new level those shrubs are overgrown and hide the windows. not a good look bring them down so that you get this look.

Is that real brick? It almost looks like some kind of panel made to resemble brick. If it is real, often they just did a thin veneer of brick on only a portion of the house to save money (as if we'll never see the house from the sides? what were they thinking?) Either way they can be removed/ replaced with more harmonious / congruous siding.... whenever it comes time to paint, not right now. If you do a pergola or new porch, keep it simple and in harmony with modest post WW2 1950s style. Your house is not the early 1900s or craftsman-esque style pictured above, and houses start looking like frankenstein houses when they have too many styles from different eras cobbled together. You should find that a lot of contemporary style will mesh quite nicely with your house - since it draws so heavily from that era. The conventional wisdom is to live in the house for a year before doing anything irreversible, but I dont that applies to tacked-on temporary things like awnings and such. Have fun!