March 28, 2026
Audit-bots vs Spreadsheet dads
Improving personal tax filing with Claude CLI and Obsidian
DIY taxes with AI: fans cheer, skeptics say “make the bot use a calculator”
TLDR: A coder used Claude and Obsidian to organize Canadian tax filing, converting PDFs and verifying numbers with calculators. The crowd split: fans praised AI-assisted spreadsheets, while skeptics warned that chatbots can’t do math without code and pushed structured tools like Superego—because accuracy beats vibes in tax season.
A Canadian tinkerer used Claude (an AI chatbot) plus Obsidian notes to wrangle tax season chaos, converting PDFs to text and double-checking the average cost base (ACB) with a calculator. They built a neat folder vault, piped docs through Python, and had Claude update to-do lists. It’s a vibe: one app to see everything, one bot to nudge you step-by-step.
Then the comments erupted. Fans loved the “AI as tax assistant” energy, with one calling it an opinionated—but practical—workflow, while another flexed a U.S. twist: Claude for Excel + an Excel1040 template shuttled numbers from 1099 forms and outperformed TurboTax. Cue the meme: TurboTax vs Claude—who wore the refund better?
Skeptics, though, brought receipts. Mic92 warned, in all caps energy, that large language models (LLMs—AI chatbots) are bad at math unless you force them to use real code. Meanwhile pscanf dunked on markdown, saying unstructured notes are a data minefield and plugging Superego for more reliable extraction. Suddenly it’s a three-way cage match: Obsidian markdown vs Excel dads vs structured-data purists. Jokes flew about LLMs being the intern who needs a calculator and checklists to tie their shoes. The takeaway? AI can help—just make it show its work.
Key Points
- •The author built a tax-filing workflow combining Claude Code CLI with an Obsidian vault to organize documents and tasks.
- •Obsidian was used for markdown notes and PDF viewing, with a structured folder layout for forms, payroll, receipts, and references.
- •A Python virtual environment (uv) with markitdown and OCRmyPDF enabled PDF-to-markdown conversion, including OCR for scanned files.
- •A custom bash function automated PDF conversion by attempting direct extraction and falling back to OCR when needed.
- •Context was provided to Claude via CLAUDE.md, which then updated PLAN.md with checklists; ACB calculations were cross-checked with an online calculator.