Back in early 2023 I tried to write a tool to do my taxes based on my broker CVS files. Since I wasn't familiar with how the data was structured, I let the LLM

Back in early 2023 I tried to write a tool to do my taxes based on my broker CVS files. Since I wasn't familiar with how the data was structured, I let the LLM lead me while building this in incremental steps. The result was not just buggy, it simply failed to detect the relationships in the data (multiple somewhat implicitly embedded tables that needed to be joined). Even after I pointed this out, it failed to handle it, getting stuck in the same kind of loop you described. To this day, no LLM that I tried passed this task of leading the development while detecting the underlying structure of the data.