The flat trim board under your windows will cause leaks if it was not flashed properly or if the sill nosing doesn't project and overhang enough for an effective drip (in the traditional manner). Sealant/caulk at that joint is only temporary. I've seen this detail cost owners a lot of money so make sure your contractor knows what he's doing. One solution is to add a projecting PVC sill nosing in place of the flat trim. It's difficult to beat the traditional double-hung window sill design. Here is a link that might be useful: ATW

From the pics that you posted, the only thing that really looks white is your garage door. Unless the whole house is in need of a paint job, I would paint the fascia a darker color. That may be enough to change the whole look of the house.

If you must paint the brick, I’d recommend a matte or satin white. You could experiment with warmer or cooler whites, but probably warmer white would be best with the terra cotta roof. you could then do a wood look paint for the garage to match a new front door. Would give it more of a spanish modern feel.

First thing I would do is make the two different brick surfaces match. The steps are glaringly different and look out of place. Or, just paint the brick steps to match the porch floor and leave the house brick alone.