Tax Return Assistant

Tax prep process modernized, as a reflection on how we interact with professions forever changed.

Today’s meditation on “what will become of the professions in the era of AI” comes courtesy of my annual family tax returns (late Feb, 2026).

On the plus side:

  • I modernized a mediocre process I’ve been using for 15+ years for collecting and processing the physical and online artifacts
  • I am giving my accountant a FAR better set of data this year, organizationally and content-wise
  • I am coming with a better set of questions and ideas
  • There are obvious ways to optimize this process further next year, including automation, all memorialized in .md

On the “Feb 2026 snapshot side”:

  • Gemini Pro 3.1 was best for parsing images of multiple receipts. It maxed out reliably extracting details of about 6-7 receipts per image. (20 receipts it still can’t do with any accuracy “naively”, e.g. using elaborate prompting – I appreciate this is an area heavily covered by SaaS).
  • Browser Automation (Playwright here) works great but, used this way, is so obviously a transitional kludge. Now it can grind through service provider sites to download docs. All those services need MCP or a CLI or .. anything an Agent can use to access the data.

On the “I oscillate between extreme excitement and dread” front:

  • At what point are am I comfortable just doing family taxes with AI?