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Nothing as sophisticated as Quicken is needed. It takes me probably no more than an hour per year total to come up with our medical and charitable deductions for Schedule A--90 minutes tops.


I certainly agree with respect to the charitable contributions; with the medical it's different. If you have enough medical expenses to itemize and deduct them, I think some ongoing analysis and scrutiny during the year is warranted, if only to monitor where you stand with your health insurance as to deductible and co-pay amounts, adjustments to/from providers, and if you've been credited for what you should be, etc.

I our family it used to be more challenging, with a daughter who had quite a few health problems. I used to keep an elaborate spreadsheet to keep track of what had been put through our flex plan(s)- and my wife and I are on different plan years, which actually helps - what had been applied to deductibles; etc. I used Lotus back in those days, except for one year I tried dBase IV just as an experiment. Switched back the next year.

I agree, things like contributions or other deductions are easy - just file them in that year's tax file. And several times during the year I will go through my check register and underline in red the deductible items, which I will recap when it comes time to do the returns.

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