Thanks! We are going to have someone other than the contractor advise us on the exterior; as soon as he mentioned vinyl siding, we knew he was great for the interior, but not the outside. This photo was just before construction began; we have already ordered new lighting and will get on the landscaping as soon as construction is finished. I like the idea of bringing in an exterior designer to guide us. The house has a lot of wonderful features (in particular, and the reason we bought it, is the lot which is 1/2 acre and at the end of a dead-end, with a large and unbuildable lot next to us). So its very private...for being in North Suburban Chicago. Any suggestions on the "monochromatic color scheme/muted pallette/various values"?

Wow, you are lucky! To have acquired the property as you described, you scored! Since you're working with a new roof, I would keep its color in mind when choosing your exterior color scheme. I would pick something in the softer, more elegant feel, like beiges, grays, soft teals or blues, greens... nothing high contrast. This would enhance the overall size of the structure. Working with basically the same color throughout, choose which texture you want to show off the most and paint it the lighter value of your palette. For example, let's say you go with a sage green in the medium to darker ranges from the fan deck of your painter. Do the brick "bookends" in the lighter value, then do the cedar two values darker. Save the darkest value for your trim. I'd probably do the chimneys in the same value as the cedar so that the color "reads" vertically. Save your color pop for the front door! Choose whichever color speaks to you the loudest and says, "Come see my awesome house!" The fact that you posted this photo during the winter months is very helpful even though it looks gloomy and hopeless at this point. This is when you can concentrate on the structure itself without the distraction of the landscaping when it's active. Also keep in mind that the house becomes its (the yard) backdrop the other three seasons of the year, so note the colors that will be blooming and the leaves changing as the yard moves through the seasons. That way every aspect works together. Again, an experienced professional painter can be very helpful. Get references, and check them all. Good luck to you!

Unfortunately painting the whole house is the affordable option. Siding will not help, it's just thousands of dollars and the house will still look basically the same so its a waste.

marzdotz is certainly right about your home and has some good ideas but here is a pretty complete summation: Lets start with the roof. Use a darker color shingle, it will give the house some weight. Do not waste your money on deep dimensional shingles. You cannot see them except from the street and with the low roof means that all you will see is the butt ends of them when you look at the house.

Paint the whole house a uniform color, it will need to be relatively dark to keep the checked wood from showing. You will need to find a professional to use a chemical stripper on your brick. Sand blasting only destroys the brick's patina and should never be done. Some people use nut shells for blasting but chemicals work best. Be really careful who you hire for this! Check numerous references because your brick can be easily ruined by an amateur. The reason I say paint over stain is that it will make the house look fresh and new. Solid stain is basically just cheap paint that doesn't have the same mill thickness as paint and has a dull dirt catching finish. Use a satin finish latex paint. You will need to prime it all (in latex) most likely for a first rate job that will last a long time. You want a uniform body color to let the house make a simple clear statement and to make the siding and brick work together. I think doing different colors for these will just call attention to details that don't need being noticed like the condition of the wood and brick.
Also I would select a mid-range color for the body because it will make thehouse look larger and you really want the height to be maximized to help offset the long horizontality . As mentioned above some natural colors to tie to all the space around it would be best.
Paint the garage door the body color as well.

For your trim use a light color. It will make the windows look larger, make the eaves feel like they rise up, reflect more light into the house and generally give the house a convivial feeling. Dark trim colors close up a house and make the overhead surfaces feel like they are pressing down on you.

A nice snappy punch color for the front door will punctuate things and give the house some focus.

Really, you are not far away from having a really attractive house.

Here are a few more shots of the troubled exterior of the ranch we are rehabbing. Another picture of the front, one side with the cedar stained dark brown, and two pictures of the brick corners with the chipped and peeling paint that we can't seem to get off.

The OP said their roof is new--so why tell them to redo it...

IF you have a computer that read Flash there are several paint programs that lets you photoshop a photo and add/change colors...

I like the idea of different textures like the brick/siding contract with a fairly monochrome color pallet...and I think the siding is in keeping with the era of the home...

Since you are going to wait to redo the exterior check out some MCM home books from library and Google stuff up--
some of it might be in b/w which won't really help with color choice
IF you go with lighter colors for the bricks on the end of the house I think that would make the house "bleed" away from the strong horizontal effect...
while it seems contra indicated I think that using a darker tone for the brick will encapsulate the house and anchor it to the ground/site...

But that is why I suggested using the photo software to try it both ways...
BM and other paint companies have those apps now--might not be as sophisticated as Photoshop itself but gives an idea...

and don't forget the brick for the fireplace that is visible above the roofline...
are you going to paint it as well?
You could also consider recladding the brick with faux stone--
something like mixed sizes of river rock or even lineal limestone in keeping with the MCM look might be options...
there are even DIY sites that explain how to do it yourself to save money...