Regular exterior paint is the wrong product to use on brick.
If you use the right product, you'll have absolutely nothing to worry about in terms of longevity.
All the urban legend nightmares about peeling brick is based on hearsay only. When it's coming from someone who has actually painted brick - and lived with it on their own house - and the paint failed, you'll find the reason why it failed if you peel into the process and product (regular paint) that they used to paint the brick.
Your house is an unfortunate combination of materials and proportions.
I totally see why you want to paint it.
Go to Romabio's Instagram page. You will find evidence of hundreds of homeowners who both hired a contractor and DIYed. https://www.instagram.com/romabiopaints/
Their IG feed of actual homeowners using and living with product goes back to October of 2016 - 3 years.
All different architectural styles, different application styles, and different colors.
Romabio has a fandeck. You have to call them and order it. Also need to find out where you can buy it. The Roma fandeck is a good place to start with colors but you can also have their product color matched to Ben Moore and Sherwin Williams colors.
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SW Grey Heron
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