Masonry Repair

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Congratulations on the up-coming marriage!
To prep the outside, rent a high pressure washer and use it to remove the loose paint. Be careful with it because is can be dangerous. Caulk cracks and blend the caulk in with a damp sponge.
You don't use popcorn texture outside, but you could do a stucco-like texture. But that is a lot of work unless you have experience with it; I wouldn't recommend it.
To do this, all you need to do is pressure wash it and trowel on the stucco patch material mixed with the latex additive instead of water. But it would be a major task. Visualize trowelling the whole exterior by hand!!
To paint the exterior, I would use a roller. A pro painter would use an airless sprayer, but that takes some training. An exterior latex masonry paint is what you want to use. Painting is not so bad a task.