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1 - Yeah I'm expecting to see a few startups doing this come out in the next few months. Very doable. I'd use embeddings for classifications of expenses (https://github.com/openai/openai-cookbook/blob/main/examples/Classification_using_embeddings.ipynb) or you could use regular GPT, too. Then every incorrect one gets fed back as an example, too. Most of the work will be around the regular software building.
You could also do a basic version by writing the topics and info in a PDF, and then uploading that PDF to this site https://knowledgegpt.streamlit.app and then asking your questions using that