I finally took this community's advice after reading about plain text accounting for years but being too scared to dive in. I timeboxed it to an hour or two this weekend and thankfully large language models are more than up to the task! If anyone has done similar things or already solved this problem I'm all ears. Next up will be a dashboard using Observable Framework with this transactions data (https://observablehq.com/framework/; made a demo here: https://jaanli.github.io/american-community-survey/income). Open to any feedback/tips if you have done this before or are less fearful of accounting!