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It's common to cut and style G4 hair to be "show accurate". Other than that I don't think most people cut hair on purpose, unless it's an all new re-root and you want a pony with a mohawk or something.
I wouldn't cut a pony's hair myself (except for making a preexisting trim look better), but I do like the character it adds when ponies with haircuts come my way! I think it makes them more unique and interesting. My g1 Salty who came to me with a haircut that I styled into an adorable choppy punk rock look is honestly one of my fave ponies in my collection