Over the years, readers learned what to expect from Joel and Paul, which gave them freedom to continue writing in their own style. I'm curious how the same writing would be received today in a very different environment - much more crowded and driven more by social media than the open web, not to mention the shift of attention towards video. I just don't think writers today have access to the attention that tech bloggers of an earlier era built up.

There is a balance. A short story can help understand. However you can go too far with stories. Joel strikes a good balance because it isn't long before you realize why the story is relevant and he cuts out a lot of details that are not relevant. He also is telling non-fiction stories, which adds additional credibility (unlike many blogs that are making up fiction stories)

I think you are getting confused with the format for the reader. Someone looking for a light read would prefer a entertaining read with the twist of learning something, someone looking to learn something will be annoyed at your prose and narration style. What you write is aimed, whenever you like it or not, to a person in a particular state of mind. The motivated to learn will want you to not tell them about your grandma when they are reading the stupid recipe.

With all due respect, PG and JS were titans of an era where attention spans were not short. I am not sure if that strategy would work in the LLM-era.