What a fantastic architecture. When you do the brick, if you stain it with masonry /concrete stain you won't have the same issues of maintenance as with paint. They will spray it evenly - through you will have to select a deeper color - either taupe (brown-gray) or a straight charcoal. Love your windows and the classic angled railing. I think a dark gray on the siding will make the orange brick jump even more. What bothers me is the white (railing, fascia, eaves) juxtaposed with the earth toned stuff. So I would recommend camel tones - for the siding - something like http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6108-latte/ and the hopsack next darker tone for the garage door. Use the lighter tan for trim that is now white - http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6107-nomadic-desert/ Use the darkest tone if you are painting concrete steps. If you think you will stain your brick charcoal, then the white eaves and trim are probably right, and you may not want to paint it tan now and then go back. If your brick were charcoal, then I would block out the rest in grays and blue grays - leave the white eaves, but take the railing and posts charcoal too. A blue gray door - like sw smoky blue.

Now for Mr 16 months... I really can't decide. His room is going to be on the cold side of the house, with not so much sun so I want it to get that cozy sort of feeling when you come into it. I was thinking yellow or orange curtains? But then I don't know what colour to do the walls. These are some fabrics I like:

The front door is around the other side by the way! The windows are aluminium so cannot be changed. It is all rather ugly at the moment.

You are so right white is never out of fashion. I would set your budget and then look at your options. If you plan to stay in the house for many years then spend to the top of your budget (if that is going to give you a life time of pleasure), if you plan on being at the home for only a short time / few years then I would go mid range so it looks lovely, will have good resale value but you can invest your well earned money to go towards something else as well. Obviously Marble / Granite is the top of the range but there are so many cheaper and very attractive options these days that look just as good.