My less obsessive personal finance workflow: I have a spreadsheet. I update it by hand once a month, and have been doing so for ~20 years. Takes about 5 minutes. I only track the categories I care about. Those have varied a bit over time, but have always included staples like power, heating, water, ISP, rent/mortgage, insurance, savings, etc. I don't track things like groceries or restaurants or anything else that I…
We track way fewer categories than you do. But in addition, we also track larger expenses by amount. Right now everything over $100 gets an entry. That means a fancy $100+ dinner gets tracked but a normal $30 dinner doesn’t.