Normally, I would say don’t paint, but I can see why you are not a fan of this particular brick. So, I say “yes”, go white and “no” to the shutters. I would love to see your windows and window trim painted a gray of your roof.

Often posted dilemma: http://www.houzz.com/discussions/query/%2Bbrick-%2Bpaint-%2Bexterior

You could try a wash first, because paint does -like feeny said- mean more maintenance. In your case I'd say a dark grey wash (=stain), because of the darker bricks (first picture below)

But, without the maintenance paint story: Using the colors from the brick as paint colors for the woodwork might turn out great too. The whites give too much contrast. (second picture)

A bit of cottage, white stain:

The risk (as in the need for maintenance): Flaky paint.

We personally have a center-hall Colonial. We painted our not-so-nice brick as well. Today, we often get offers to buy our home. We also beefed-up our wood columns. It's beautiful! I'll send pics soon...

Look at "dye brick" products as it will require less upkeep. Another option would be to parge the brick or white wash. I'll dry to find some pics.

Here are some brick wash photos. Can we get a photo with a wider view? There is a great deal you can do to add curb aooeal and instant equity.

Thank you all for your input! The brick has been plaguing us since we've moved in. I am not too fond of some of the stains I've seen, but the whitewashing idea isn't bad. My only concern with whitewashing, however, is that it won't look the best with the bright red/orange brick I'm working with. What do you think?

I have painted brick. It was painted by the previous owner, and I repainted it this summer.
It's all about prep. Hire a reputable painter or do your research if it's a DIY. Have to agree with you on the brick you have, it's not so pretty and deserves a chance. The color I used was SW Sticks and Stones, a beautiful mid tone taupe. Black shutters would work very well. I have white trim and a black door.