IMHO, the way to cure a houses identity crisis is not fight it, but let it be what it is! Which in your case is a handsome solid-looking midcentury modern... or lets say within the genre anyway, if not a prime circa 1959 specimen. Definitely has that cool ranchy kind of look and a lot of current fabrics, doors, furnishings, color palettes etc are straight out of MCM which means they would fit right in with your house. Not that you want to go over the top with making it into a time capsule or shrine to MCM style, but just let it influence/inspire your choices. This door fer instance : http://www.homedepot.com/p/Builder-s-Choice-36-in-x-80-in-Atlantis-3-Lite-Clear-Glass-Painted-Fiberglass-Prehung-Front-Door-with-Brickmould-HDX162460/204843729?&cm_mmc=Shopping|THD|B|0|B-BASE-D30+Doors|&mid=ex1mxG05|dc_mtid_8903vry57826_pcrid_73667292101367_pkw__pmt__ Sorry, but adding early 1900s craftsman brackets and other elements would add to an identity crisis, not cure it .... As for color, people were not afraid of color then! OK, so you might not want to go vibrant brick red, or avocado green, or chocolate brown but even if you prefer something more contemporary, ie really grayed out or neutral, at least go darker and richer to give it a more solid look as well as fit in better with your beautiful woodsy natural setting. Re symmetry, agree its not necessary..... but it should and I think does have a well balanced look. as I recall from (long ago) design courses there is formal balance and informal balance - both are good, and again I would just go with the original design intention.... if it works, why mess with success? The garage on left nicely balances window arrangement on the right, IMHO.

Powerwash YES. Paint brick NOOO! Tudors have natural brick or stone and dark wood for the half timbering. Some, called magpie houses, in England have Black painted timbers and bright white stucco. Dark brown trim wood and cream faux stucco siding is appropriate for a 1970s Tudor. If you paint the brick and trim those light taupes or grey you might as well add shiplap and call it modern farmhouse. Really it is your choice if you want to keep the classic Tudor look or follow the latest trends. Powerwashing and some tree trimming will brighten it a lot. Then add some flowers for color.

OP, as I said, the "drapes" wouldn't be nearly as overpowering as the photo I showed...and they don't need to be so full or high... If you don't have room to move the armoire, then it's staying, so how about that small area with the octagonal window becomes a "dressing" area...you could have a cheval mirror in front of the window (won't cut off all of it I imagine) and the wall could hold scarves/necklaces/purses. OR you could have a dressing/makeup table under the window and a little fancy chair...in other words, give that spot a purpose so that the window doesn't look like the odd man out...

NNo shutters and IMO no window boxes this is a contemporary don’t mess with the style . You have space bewtweeen the house and the drive way to landscape are those panels at the front in the garage area? This is one of my fave landscape ideas usually for a MCM house but I think it has great ideas for inspiration with your house. Since the windows need replacing I would do black ones and no grids