But it seemed like a lot of people overlooked why it was loved. Most of us weren't wishing that our 2k+ line projects were all written in it.
Those little 20-500 line scripts were just so much more fun in Python than anything else though, and it showed up in survey after survey.
It's notable that you've written this in the past tense. These kinds of scripts don't seem to be a focus for Python any more.
In fact, I recently heard as justification for a new Python feature: "it helps us with our 100-million-line Python codebase". The language has become extremely complex as it prioritizes the needs of a few teams writing millions of lines over millions of developers each writing relatively few lines.
The reason is that the design team are all working on these large codebases and, understandably, mostly focused on what makes their own lives easier. I was hopeful that in the transition from a BDFL-based governance system to a Steering Council, we would see a larger variety of experience and opinions designing the language. Instead, I don't think there has ever been a single scientist, finance worker etc on the Steering Council - it's always software developers, almost always employees of large software companies.
The other obvious example of complexity is pattern matching. The feature is very complex, especially how it breaks established rules of the language. It also required fundamental changes to the interpreter to accommodate it: a rewrite of the parser from simple LL(1) to PEG.