I don't know whether this is just nostalgia, or maybe my finances used to be less complicated, but nothing beats the experience I had with the Microsoft Money desktop app.

It was easy to download transactions from participating banks (I think in OFX format?) and it was easy to see the last successful sync date per account. The UI made it straightforward to categorize my transactions and dead-simple to compare monthly spend against an easily mutable budget.

In fact it was so easy to use that for a good long while I found myself manually entering cash receipts and even tracking my cash purchases. And it cost $0. It felt better than Quicken for personal finance.

Maybe I have missed some major innovation in personal finance software -- I largely use Mint and home-grown spreadsheets now, and I keep hearing that people use paid tools like YNAB or free complementary-to-the-company's-real-job tools like the Personal Capital suite -- but this all feels like it's worse now.