The stained wood should be restained in the same color. The wood trim can be painted a traditional woodsy color such as dark brown or forest green. Gray has not gone out of fashion yet in some areas, but it might look like catching the last of a trend.

Agree that this wood (siding) needs to be stained, not painted. Could however be a grayer weathered wood color. A much larger range of exterior wood stains than there used to be! Then for trim choose an opaque version of the same color (or paint to match if it cant be stained). Plenty of visual interest on this house with alll the different textures of the natural materials - would not break it up with different colors. Blue gray and/or white for door, accent colors.

Will the white windows stick out? Any options for them apart from replacing? Are you able to share inspo photos?

SW Polished Mahogony