Hi, Kwelch. You might want to think about painting your brick. One of the benefits of a brick house is that you never have to paint it. But once you do, you can plan on repainting it every 5 to 10 years. And once you paint it, it is almost impossible to remove the paint. You will be stuck with it forever. While this might seem to be no problem to you, someday your house will be sold. The paint will tremendously affect the resale value. Before, you had a house that never had to be repainted. Now you have one that has to be. With the way most people think about home maintenance, what do you think this will do to the value.
As far as painting the shingles, there are some coatings that are made to extend the life of shingles but I do not know of any that are colored. And painting with normal paint will quickly end up in a big mess. Much better to reshingle. Henry in MI