Googled the karaka tone - consider resene ash - closest to a creamy white when you see it on the exterior. Depending on your house style, (more cottage like) I'd contrast the karaka green with a near white tone rather than a khaki tone. More modern, more khaki.

A green roof pairs well with gray and white homes. For a subtler look, pair a green roof with a siding in a lighter shade of green. I think you are on the right track .You have chosen harmonious shades . New paint doesn't have to match existing colors, but it should harmonize. Some general tips are- Green roof - Gray, green, or white house colors. You could use a dash of yellow also.

There are different kinds of ivy and plant privacy screens that can be purchased which might cover your fence and gate and give you the privacy you are looking for. I have not used them before but the photos look very nice. If you picked a color to match your side or front bushes, it would look very nice and becost effective as well. You have a beautiful home. Good luck and please post photos of the final.

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.