u/NickFromNYC123

I was wondering if anyone could recommend a system that could take all of my transaction history from Webull and organize everything into lot-level data, with the ultimate aim of optimizing taxes by tracking cost basis and holding period. This is somewhat complicated by the very high volume of trading I do.

What I've tried so far:

- Downloading stock and options history from the app as csv files, and then uploading those csv files to an LLM (have tried ChatGPT, Gemini, DeepSeek)

- Prompting the LLM to create a spreadsheet tracking all opened and closed lots (using FIFO logic) to yield a page of all currently open lots with cost basis, days held, unrealized gain. Have also added a wash sale tracker for adjusting cost basis, and it pulls the current stock price from Google Finance for calculating unrealized gain.

- Manually adjust outliers like exercised options and stock splits

The problem:

- The LLMs, 99 times out of 100, make errors with this. Maybe because there are too many lots it's tracking (10s of thousands), maybe I'm asking for too much manipulation of the data.

- Asking it to take the spreadsheet and fix specific mistakes usually creates a slew of new mistakes

- Even if I get it to create a workable version, trying to update it with new CSVs of more recent transactions tends to create lots of errors

I'm not very educated in software or using AI agents. Does anyone know of a system that could either interface directly with Webull (app or website), or that could accurately digest the CSVs to organize this data?

Thanks in advance

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