I use Simplifi Money. Yes, it's Intuit. Yes, Intuit sucks. That's the system though. They have the best bank integration. I've used others like YNAB and a few c

I use Simplifi Money. Yes, it's Intuit. Yes, Intuit sucks. That's the system though. They have the best bank integration. I've used others like YNAB and a few competitors. They aren't as good. You cannot get out of manually categorizing everything, but the transactions use regex for auto categories so that reduces some work. Once I approve all of my expenses, I go into Simplifi's spending plan and I make a plan for large one-off expenses (roof repair, new tires) for the month. These are added to a copy of the spending plan from the previous month. What this does is leave you with the transactions that are "unplanned". I check those and I add anything I missed to planned expenses, or I dispute those charges. It works extremely well for me, and I balance a large number of accounts. The only issue is that it doesn't work well with investments. For those accounts I keep a separate spreadsheet with a column for each month. I put balance and returns for that month as well as returns minus Inflation month on month. Every three months, depending on my income stream, I may deduct some money from investments, but the rule I use is I only deduct a positive 3 month return - inflation over that period. That way I only take money out of the market when it's up. The system works well for me. I should also say I keep a 3-5 month buffer in stablecoins on Gemini. I earn a relatively nice return 7%-ish on a very liquid asset that I can draw from within 3 days. I also keep 1-2 months of expenses in my checking account.