1. What automation, if any, exists for entering transactions? This is the most laborious/cumbersome part of personal finance. Some tools use financial data aggregators (plaid, yodlee etc.) that involves sharing login credentials with a third party, sometimes disabling 2FA, or other steps that are anti-security or anti-privacy. It sucks that in the USA at least, there is practically no way for customers to fetch their bank data via an open API. Until recently, many financial institutions supported OFX, but that is being phased out.
2. How is categorization of transactions accomplished? Ideally, I want autocategorization based on my own previously categorized transactions, since the bulk of my transactions are repeats at the same merchants.
3. What sort of reporting, dashboarding, and potentially sharing capabilities exist? Ideally, I want to share some reports with my partner
A while ago, I created my own homegrown system to automate my personal finances[1]. It is capable of doing all of the above, without sharing data with a 3rd party. Unfortunately, the automated transaction retrieval mostly does not work because financial institutions are dropping support for OFX.