[emef]

I track account balances once a month into a spreadsheet to keep a high-level overview. It's a manual process that takes ~15 minutes and has a large payoff to have a birds-eye view of all the finances and allocations.

Investments are all automatic: max 401k, max hsa, auto deposit to vanguard into a few indexes. If cash balance gets too high, I'll do a manual deposit.

My wife and I aren't big spenders so I have never found much value in micro-managing individual purchases or categorization (YNAB or mint). I do skim the transactions a couple times a month to make sure there aren't any surprises.

wrt paying off loans vs investing: lots of approaches here, the emotionless take is to just allocate based on interest rate. If your loans are low interest, then just pay the minimums and invest the rest. If they're higher interest than you expect your returns from investing to be, then just pay them off aggressively and don't invest at all until they're paid off (the exception here might be tax-advantaged accounts like 401k or IRA if you qualify).