I think a light grey would look very smart - white trim. Be sure to paint the garage door the same color as the house to help it disappear.

Where do the doors go - into which rooms? Was perhaps the side facing the driveway meant to be the "front," entering into your front room/living room? Sometimes they placed houses in a way that might have made sense at the time, but don't anymore - or rural areas the house sometimes faces driveway instead since no one would be approaching from the front. I would not be spending money on adding on dormers and other stuff not original to the era of the house. Sorry, like it or not, its not a colonial or cape house.... but it does in fact have a charm or character of its own. Sometimes with an old house, less is more. Be careful you don't ADD to the visual clutter already there, and instead, you want to strip OFF the extraneous gack that is creating visual clutter - like the 2 extra porches on the driveway side! LOL - its like you have the orginal sunporch, then another porch was added on to that, then the third porch (with stairs) onto that! Do any pics exist of your house in the past? I wonder if there wasn't a porch on the side facing the street, with the roof attaching to the wall in that blank space above the door/windows and below the eaves. Rather than dormers, spend your money an open porch - need not span the whole length of the house, in fact it might look best just putting it on the right side over door + 2 windows to the right. Duplicate exactly the pitch and style of the other porch roof. I would make it an open porch, then your landscaping- flowering shrubs and ornamentsals in front of porch with inviting walkway from the street.

I think a cream paint colour would go well with your roof tile. And I would go with all wood accents. Wood shutters, wood posts, wood front door, wood garage door. Paint your white trim dark brown or a colour close to wood tone and paint your window trim black. The posts need to be bigger and chunkier. And you only need 2 instead of 3 if you go bigger. I didn't have time to add landscaping to the pic but add BIG pots of planters to the porch area and add a garden in front of your garage. I would remove the small triangular garden on the left side of your driveway.

Gray/charcoal would work.