Thanks! I think the trim at one point was a chocolate brown, because I can see remnants of it on the brick in a few places. We think we do want a color that's not brown/beige/tan/white -unless that becomes the best option, because we've always lived with those colors in former houses, and just feel like the exterior could be turned up a notch with something different. For a red door, I was thinking a deep cranberry color. DH still wants something brighter. I'm afraid that the brick, roof, and surroundings can't support a bright color.

I love crape myrtles and have several, but they can be a nuisance too close to the house like those are. They also have very extensive root systems which don't allow for anything growing nearby, especially after they have matured. These have been allowed to grow too many weak trunks and, if they remain, should definitely be trimmed to around 5 main trunk stems. Instead of a single front door with sidelights, try a double door and beef up the entry, maybe with a transom above. Right now the double windows in the front seem to be the prominent feature and detract from the entry. As to the color, knowing you need to keep the white window trim, I'd like to see a mock-up with something darker and as Annie suggested a beefier window trim in a contrasting color.

No white stain, no solid gray stain. As others mentioned, replace the random wood boards with redwood. If not possible, then work with those boards to stain the to match the house. Does the siding ’need’ to be restrained or are you doing this because you want to change the look?

Looks like the Tudor detail above the large front window is actually built into the brick application, so ti may not be wise to remove it. That is also commonly found in the gables of craftsman style homes, so I wouldn't worry about it if it is recessed into the brick. The brick behind it may reveal just how the original brick looked, and you might not want to deal with any color difference. If you want a less rustic/chalet look to the home, change the siding from B&B to horizontal. Have you thought about what you might do with that smaller bumpout window on the last photo? That gives it a chalet look to me.