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

3 pointsbrianhorakh1y ago3 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?

3 comments

LinuxBender1y 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.

brianhorakhOP1y 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.

dinkumthinkum1y 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.

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