A pergola will obstruct light into the structure. What is the structure used for? How do you plan to use the deck for? Eating? Sitting? etc? Plan the activities and the furniture you'll need and draw up a floor plan. Floor plans are important outside & inside. The steps to the deck from the lawn are a little too abrupt. Needs a transition. Consider adding cement pavers to the grass, not as an extra patio but for a nicer transition design.

To answer your question I would paint the body of the house blue, all trim white, and then the "fringe" which I think ties into your porch decking, I would paint it the gray. It is a good "grounding" color for your home. Sherwin Williams has a cool web tool. Take a pic of your house and load it onto their site. You can "color" away on your house. When I painted my house for the first time, I did not want the garage door to stick out, wanted it to blend into the house. Everyone said it would look weird, needed to be painted the same as the trim. Used the Sherwin Williams site and realized want I visioned looked good. I have neighbors of dubious design skills! Ha! Ha!

Thanks for the replies! My wife suggested we talk to a local real estate agent, so i think that is a good idea... just that Im not sure how helpful they are likely to be if we arent selling yet :) As for saving for our dream house, I dont disagree, however if doing this up nicely over the next ~5 years or so while we live here nets us some extra in the eventual sale, then that of course will help us as well. Interesting thing happened today actually. I got a knock on the door and one of the older neighbours asked if he could take some lemons from the tree. I of course said yes. Anyway he was telling me he had lived in the street for 40 years. I asked him if the house had always looked like this, and he said no that ~30 years ago the old old owner did a massive renovation and pulled off the timber and put up the bricks and gutted the inside of the house. Interesting stuff!

Nobody's asking, but I wonder what a wood garage door would look like, something to bring out the bit of brick at bottom....I liked our split level.