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I decided to have a crack myself and see what come back.
Here's a few names / blogs that might be useful:
Chris Olah: He's written extensively about deep learning and AI. His blog, colah.github.io, has a unique graphical style that helps explain complex topics.
Distill.pub: This online journal publishes clear and visually engaging articles on machine learning topics. Some of the articles have been discussed on HN.
Andrej Karpathy: Director of AI at Tesla and previously a researcher at OpenAI and Stanford. He's known for his blog, karpathy.github.io, where he delves into various AI topics.
Ian Goodfellow: Known for inventing Generative Adversarial Networks (GANs) and for his deep learning textbook. He might have some writings that match your description.
Ben Recht: A professor at Berkeley who writes about the challenges and misunderstandings in machine learning on his blog, www.argmin.net.
Sebastian Ruder: He has written many articles about NLP and machine learning at ruder.io.
You can also try searching via https://hn.algolia.com/
Several years ago on HN there was a blog post which (attempted to) answer this question in detail, and I have been unsuccessfully trying to find it for a long time. The extra facts I can remember about it are:
* It was by a fairly well known academic or industry researcher
* It had reddish graphics showing slices of the problem domain stacking up like slices of bread
* It was on HN, either as a submission or in the comments, between 2016 and 2018.
If anybody knows the URL to this post, I would be stoked!