I manually enter every expense (as categories are not by store, so automation can’t work), and YNAB makes this more convenient with a lot of tiny things (though on testing, the biggest parts are probably remembering the last category for a payee, and better flowing "enter"-key behavior when entering multiple transactions).

That said, it also has a bunch of things that I’m missing in YNAB, so I should probably just set up an instance and go a week with trying it, so thanks for the nudge :)