Hi, I need some help from you awesome people deciding color for our house and a complimentary door color. All help will be highly appreciated. thanks.

I have no idea if this is a possibility, but have you checked to see if a contractor could sandblast the paint off? Even if small bits of it remained, maybe it would have an antiqued effect. You could seal the cedar shakes. If that does not work, I think that "block from the beach" factor is the deciding factor. maybe driftwood or sand dune or saltgrass color. I would keep the wrought iron railings, and just paint them if they look too stark with the new paint color. Door and shutters can be painted once you see how the house looks with its new paint job. It's a lovely lovely house.

Do you think the photo may be dark and gloomy?

Pretty house! I actually like the current siding color and think Oyster Bay would look good, too. The current siding color is nice with your roof color, and OB would also work. The black shutters look good and so would Iron Ore. Kind of win-win for you IMO. :-)