No. of Recommendations: 2
If you want to download transactions, you'll need to re-buy the program every year.

This is not true of Quicken at least. I am still using Quicken 2004 and it downloads my CCs and investment accounts just fine and I am not aware that it will just "stop working" any time soon. Perhaps you are thinking of Quicken changing data formats (and banks adopting it). In the past few years Quicken's data format changed from QIF to QFX. Banks and CCs followed suit and some stopped supporting QIF after a while so if you wanted to continue downloading you had to upgrade to a more recent version of Quicken.

Also, Quicken 2005 and later drops support for QIF altogether so I suppose I need to check the financial institutions I use and confirm which format they are using before I upgrade ( I was considering it this year, but if it turns out some of my accounts still use QIF I will probably stay with 2004 another year.

For the record, I tried Money a few years back and was unable to get used to Money's presentation of my data (I used it for a whole year, mind you) and I went back to Quicken the next year.
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