I'm pretty boring and bet I don't use it remotely as the robust tool it is.
I have (after many iterations and versions thereof) finally figured out the categories that make sense to me (happily YNAB lets me change things retroactively, so the data is not lost). I budget each month based on the month before as the starting point, then I tweak knowing what the month will hold. For example, when we drove to Texas from Virginia and back, I upped our gas budget since we'd be using way more gas than our usual commute-3-miles existence.
I like that it learns and applies categories. All of our entries from a certain company go to boat maintenance, as an example. I manually input everything so this is helpful. It also saves companies so when I start typing in say Exx . . . it gives me options of places I've spent money.
I go through credit card statement and bank accounts every week, adding in expenditures every Monday. I really REALLY appreciate the manual aspect I've chosen and would recommend it even if you have stuff hooked up; just today I caught a withdrawal from a club we canceled our membership at last year. Because I check and input every week, I caught this and have started the process of getting that money back. It took a little while to set up but now the data entry (as it were) takes about 10 minutes each week.
I set up targets for annual expenses (house insurance and taxes which come in a big lump once or twice a year) so each month I'm putting money into the category; when it comes due and it's paid, the category is back to a good level which gets added to each month. If this makes sense.
You can do a free trial of YNAB, which is nice. That said, there is some work to do on the setup side, which once you've done you might be reluctant to bail out.
