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!

As you rethink adding a fixed window, consider either a fixed window that is the long horizontal kind over the shower/tub surround and/or an octagon one with stained glass for the dressing room. https://www.google.com/search?q=images+for++octagon+windows&biw=1366&bih=673&tbm=isch&tbo=u&source=univ&sa=X&ved=0CCIQsARqFQoTCOaJ69fb28gCFcYVPgodogsLDw You could add a couple of pairs of shutters to create a pair of faux windows that look as if the shutters are closed. If you don't want a window that opens on that wall, you might consider having a fixed window and shutters that are louvered to let in some light while protecting your privacy. You might also consider a faux gable with a faux window, perhaps functional as part of the venting system for the bath.

This made me laugh: http://www.theguardian.com/environment/2016/jun/09/seagull-turns-orange-after-falling-into-vat-of-chicken-tikka-masala I couldn't copy the picture, but it's hilarious.