Ask HN: Anybody using AI tools for taxes this year?

3 points by brianhorakh 1 year ago | 3 comments

Yay! it's US tax season again.

I'm a US citizen who has moved out of the US but still needs to pay/file taxes (despite living abroad for almost a decade, having left immediately after Trump 45 was elected).

I have US investments, mortgages, bank accounts, coinbase, etc. and I find downloading and auditing each of them tedious and a waste of time each year. Like many here I have mild ADHD and when that is coupled with my feelings on the US autocracy it triggers depression. The toil of performing US taxes creates an intense emotional pain -- and like any dev/ops person I want to find a way to automate. I thought this would get easier as the years passed but it's actually gotten progressively worse each year.

Being offshore I experience wildly different targeted advertising and have no friends/social group (beyond HN) to seek advice from.

What (if any) open-source AI tools exist to speed up parsing the data, generation of reports etc. I'd prefer CLI and OSS tools that don't require subscriptions. CLI/TUI preferred.

Examples might be converting PDF's to CSV using OSS, but what else (ex: categorization, expenses, summaries), agentic workflows, etc?

Due to complexities of being offshore I use an accountant who specializes in ex-pat. I don't think software like quicken will be helpful (please correct me if I'm wrong).

Others in similar circumstances what tools do you do to make managing US financial accounts & taxes obligations less tedious/painful?

LinuxBender 1 year ago |

I can only speak for myself but I would never trust LLM's to do anything that required accuracy or understanding the nuances and ever changing details of the US Tax Code. If I were an ex-pat I would send all my documents to a CPA in the US to process and file on my behalf.

brianhorakh 1 year ago | |

To be clear: Not looking for an LLM to give tax advice (very cringe!) .. although it might be entertaining.

Yes, I do have an expat focused CPA based in the US who ultimately calculates & e-files for me, and however she has a questionaire and still requires me to prepare a summary.

She doesn't correlation transactions to acocunt codes which tend to be very repetitive. In my case many recurring & usage charges on different cards, etc. that need to be categorized, summarized.

As a consultant I've designed and implemented several big data systems which use various ML OCR in workflows. I'm referring to the toil of converting statements from PDF & classifying the receipts.

I'm not especially worried about an LLM hallucinating because I can/could objectively check to make sure the math adds up. If it gets a few categorized incorrectly then it's not the end of the world because mistakes happen -- even with humans. I will still need to audit it at the end.

Even a system which could get 95% correct would potentially reduce my toil from a week+ of emotional pain to a few hours. I wager a model with a fresh context performing a single line item with examples would outperform a human.

This is not something I necessarily need to solve this year .. for now I'm going to have to pay taxes every year until I decide to renounce my US citizenship and that also requires liquidating retirement accounts etc. with severe penalties & horrible tax implications.

I'm not super old, so there is a range let's say 1-50+ years ahead of me (given my age, when I will die) so an effect of automation could be to add a week a year could potentially give me a net result of an entire year. It might also have ancillary benefits of reducing both stress and inflammation, lowering cortisol, etc.

dinkumthinkum 1 year ago |

Have you ever thought of just hiring an Enrolled Agent to do it for you and be done with it. Talking about the “autocracy” and all that, I feel like you might just be way overthinking this. It’s not that expensive if you’re making all this money.