I've gone through a few applications/services like this - YNAB, Mint, and a handful of Mac App Store applications that tried to accomplish more or less the same thing. They all requested some sort of subscription or hit me with ads every chance they got. Auto-import features usually end up being lack-luster for me as well, forcing me to log in every time or something along those lines.
I've come to realize that for the gainfully employed, above-average computer user, Excel/Numbers/LibreOffce (but mostly Excel because of PivotTables) is probably the way to go for a few reasons:
- You're looking for a post-mortem/retrospective on your spending as a way to adjust habits accordingly, not a way to pay off huge debts (YNAB is actually quite good for this latter part, but that's not what I'm looking to do)
- You don't want some program's buggy workflows getting in your way when the data is /right there/ and basically just a table of CSV values
- You want custom reports, charts, and other things
- It's just really not that hard. Any bank will allow you to export financial data in CSV or a similar format.
I just export my data every month and do a post-mortem. Easy enough. No extra cost.