What kind of a budget do you have? Do you want ideas for a pro or do-it-yourselfer?

Well Kelly, you have what we here in Wisconsin call a Rambling Ranch. In the 50's, 60's and 70's, the emphasis was on horizontallity. There for you have low sloping roof pitches and strong horizontal lines. Today's residential design focuses more toward vertical elements and broken roof lines. Multiple gables for instance. In your case, that stuff would require doing major surgery, something I'm sure your not ready to tackle at this time. Try a nice coat of paint with contrasting trim colors and perhaps some columns in the center section with emphasis at the door. A trellis or small roof addition. Redoing the landscape with some flowing beds coming out from the house will help to break things up.

That she is! I definitely think any major construction out there will have to wait. So with that in mind... To paint the brick or not? If not what colors will best compliment that particular brick?

The brick looks good with the roof. I would paint the rest of the house rather than the brick.

for starters: PLEASE do not paint the brick. it's beautiful. i see 2 "seedling ?" trees that are way too close to the house mostly because their root systems are going to cause you all kinds of grief & the shrubs are too close to the house for being the size they are; those big shrubs would look better near the curb. i'd dig up the trees & place them more in the center of the lawn---one on each side of the sidewalk. i really love a curved driveway & your property can totally handle it & will look much "classier" than a straight cemented driveway + cement pad. i like the colors you have.