WakeGal
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The important part of painting brick, like painting anything else, is the prep work. The brick needs to be clean and dry before painting. Also make sure the mortar joints are tight before painting. If not, or if some is missing, caulk before painting to fill in the holes. If the mortar is sound, a power washer may help a lot in the prep. Make sure you get the efflorescence (white powdery stuff) off the surface. Latex primer, maybe two coats. Exterior latex paint. As noted above, unpainted brick will soak up a lot of paint.
As for DIY vs hire someone, it really depends on your appetite for work in doing proper prep, and the difficulty in reaching all of the surface you want to paint.
Interesting! We're looking at a few homes and that is one of the improvements that I'm thinking about doing. I even know what color I want to do it in. My husband thinks he can DIY but it will require a lot of time. I'd rather just hire someone to do it.
I have seen exterior brick painted on a few occasions, while the workers are painting. It didn't look like a difficulty process but what I always see is the annual touch ups.
My next step is to find a painter and get the job quoted out to see if it is something that I actually want to do.