Blue gray window frames match the funky roof. The cedar is diametrically opposite on the color wheel as a orange tone. Usually the browner grays (sort of the light shade now on the stucco) do better with cedar to say modern, but since you have the blue gray, allow me to suggest that you just go as dark gray as you can - nearly charcoal on all the weatherboard. If you are in a high heat area (palms might or might not be - that might be the ocean on the horizon which might me an onshore breeze all the time) then you want a white. Not a blue-white but a warm white - bm maritime white is a good choice. With the cedar and the two blue-blue-gray elements, you need neutral without tone.

paint the pergola. frame out the windows and paint those leave the house white and add some colorful pots and some patio furniture. where is this house?

This is why it's always good to have a pro to hold your hand for at least some of the way, (carefully chosen though, check out his/her finished projects, the more varied the styles, the better she/he will be able to understand and adapt to your desires), they can provide the invaluable visual supports too. When it's your own house it's notoriously difficult to see the possibilities, you have it under your eyes the whole time and the defaults shout at you and prevent you being able to see it objectively and envisage the possibilities. you're emotionally involved and emotions always have the upper hand on the brain, so you just keep turning round in circles. Something akin as to why a psy must never attempt therapy on a member of his own family, if you follow me :D As for the façade color, are you sure it needs changing that much ? Once those thick white frames have gone and the new windows nestling more discreetly, correctly positioned and re-proportioned, the aspect will change drastically and be far more streamlined and modern. (the devil is in the detail) I'd also strongly suggest that the wood facing just breaks off around the windows, no framing or finishings. Same thing for all the windows, the small ones too. Entrance : Same as for the windows, that outer frame shouldn't be touching the ceiling, you can try taking that off and painting the door another color before deciding to change it and once again the door could do with setting back a little. You could maybe take that doorstep out while you're at it. Also, i don't know what is happening to the right of the door but i see the concrete steps leaing up and feel it would be good to create another level to make it flush with the bottom of the door if structurally possible. This would tie it all in better and you probably wouldn't need any additional definition to your entrance. Anyhow, as i often quote, i'm a firm believer in " Less is More " , and vice versa of course ^^ Question #4 i can't answer as i haven't really understood the problem And #5 i don't think so, but once the other transformations have been taken care of i think you'll find it speaks for itself. Whatever, it's a very exciting project, the bones are great and i'd love to see photos of progression once you get started.

I understand going with the grey since it is an 80's style house. You could also do bright bold colors. I do not know if that is your style. I have attached a quick rendering of the gray scheme you mentioned. I prefer light colors above dark colors. This keeps in theme with the sky and earth. Makes the house seem more grounded. The dark entry also draws your eye to it especially with the light coming from the other side of the house. I have also attached a quick rendering of a blue scheme. It looks like you are on a beach and I thought this would blend in with the surroundings. If that is what you are seeking. Hope this helps.