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I happen to hate Quicken (YMMV), so I use GnuCash. But even a spreadsheet can manage this. One column for income, one for charitable contributions, one for medical expenses, etc.

I never found Quicken that useful for imports into TurboTax. It always screwed up, and it was difficult to fix the screw-ups.

One year, it renumbered all the categories internally (probably a program bug), so every category was off and put the amounts into the next higher category. Intuit's help was useless. They said to reboot. That did not work. They said to reinstall Quicken. That did not help either. They said to restore from backup. I had daily backups for the previous week, weekly backups for the previous month, and monthly backups for the previous year. It turned out I had to use a backup for the previous year, and they thought nothing of telling me to just enter all the transactions for the previous year. About then I switched to GnuCash. And a few years later, I switched to TaxAct. So I am through with Intuit.
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