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Context is everything.

A twee handwritten sign for free range eggs at the roadside is likely to do well.

A handwritten sign for flying lessons on the other hand..

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And anyone selling flying lessons could probably afford a graphic designer, it sounds like we agree.
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Now that you mention it, I'm pretty sure I recall a hand-painted "Skydiving" sign at some small rural airport...
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Prompt: make me a poster in the "looks like garbage made by someone who doesn't know how to use Microsoft word or what aspect ratio is" style...
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