oh mate, i feel you so much on that "every weekend is tax season" grind. what finally clicked for me wasn't some fancy automation stack - it was just lowering the bar on what i actually needed to track. i slimmed down to one checking account, one credit card, and started caring about only three numbers each week: cash in bank, net Stripe inflows, and upcoming annual renewals. That's it.
For the actual categorising, i dumped Stripe + bank transaction feeds into Wave first, then moved to Xero when things got busier. i blocked out a fixed 45-minute window every Tuesday to reconcile the past week. Stopped obsessing over every failed payment - instead built a simple dunning view inside Stripe and kept a monthly "churn / at-risk" note in Notion. light structure, weekly rhythm, no perfectionism.
On the lead tracking side, i went through a few community monitoring tools (Orbit, Hootsuite) but ended up with Pulse - it quietly surfaced threads where people were actually turning into trials, without me having to patrol forums all day. same philosophy: ruthless simplicity, consistent cadence, and forgiving yourself for not automating everything immediately.