I don't necessarily agree with your architect about the trim because IMPO the finished product is a package of varying elements not just one color. The white trim may represent cottage to him just as the color your son & husband love represents southwest to you, but if you look at inspiration photos, sort through homes on Realtor.com or even drive around your neighborhoods, you'll see that the color is only one part of the finished package. I think you'd be best served by visiting a Benjamin Moore store with a photo of your house in hand. Look at the colors in person that you and family seem most drawn too, ask the color specialist there what he/she would recommend as a palette for the colors you like, and then get samples. You're never really going to know until you see them up close and personal.

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.

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?

I love that current yellow! It’s so pretty. Is a paint job actually needed, or you’re just wanting something different? Lots of nice ones here: https://www.houzz.com/magazine/appealing-color-palettes-for-colonial-style-homes-stsetivw-vs~72494535