The best way I've found to design software is to get it totally wrong on the first try. Once you've seen why the obvious approach won't work, and how ugly your naive workaround is, you sleep on it and a better solution will present itself in the morning. Just make sure you do this in small chunks, or the epic rewrite will take you forever.
Actually, this is the only effective way I've found to design software. :blobcat_mlem:
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