This makes me really happy to see. For whatever reason analyzing finances is enjoyable in a Civ-ish way though I never would have made the connection. A couple

This makes me really happy to see. For whatever reason analyzing finances is enjoyable in a Civ-ish way though I never would have made the connection. A couple of things I've noticed as I've done something similar: 1) Categorizing the little things as you go along was way too tedious for me too - even in really stripped down form. I really like the idea of categorizing All The Things though. How I dealt with this was to download 90 representative days worth of credit card history into LibreOffice and remove all of the "still gets paid even if I'm cryogenically frozen" payments. I then manually categorize everything that is left (quick because the categorization is batched up and auto-complete works wonders), divide by 90 and generate a pivot table that shows the daily sum of each of the categories. Where I think we diverge though is that rather than trying to keep this snapshot up to date, I just make a mental note of it as "Okay, I average $XX/day on everything else". As long as you know your starting CC balance then it's pretty easy to figure out how you are doing for the pay period. Just a matter of $start + $daily_cc * $days. 2) Kinda similar to the web app (in spirit if not functionality), I set up a little Python CLI tool that simulates my recurring expenses (along with my recurring $XX "all other crap" fund from above). Once you've set up the recurrence relations you can step through two weeks at a time, pausing to change state, transfer money, etc. It's basically like using a debugger which is an enjoyable way to test out various ideas you have that's a little bit more freeform than a spreadsheet where its hard to see how various ad hoc tweaks layer on top of one another over time.