I hated Mint, and Quicken, and Microsoft Money (back in the day), but for us YNAB really nails the sweet spot. It empowers you with your money without bogging you down.
For purchases, I put in less than one minute per transaction (for data entry). For bills, I set them up as recurring scheduled transactions on the same day of each month. I then verify them when they become current, shifting the date or the amount as needed, takes a few seconds for each one. I've done the same with my income (reliable, salaried, paid bi-weekly).
I only track cash assets and CCs. My investments, retirement accounts, and other assets don't get tracked because I don't consider them part of my budget (though contributions to them are). So once a week (more early on, getting the hang of things), I go to my bank and CC websites and make sure I haven't missed any transactions, clear all the ones they show as cleared, and reconcile all accounts. This takes less than 5 minutes per account if done this frequently.
All told, I'm probably spending less than an hour a week in YNAB, and half of it is updating the budget itself as income comes in and needs to be allocated, or verifying that I have the money before making a purchase.