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When do you know if you should Itemize your Deductions?

Is it safe to Itemize or just keep it federal like its says there "Recommended"
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When do you know if you should Itemize your Deductions?

If you wish ,you can enter your itemized deductions. Once you have entered all of them and clicked on "done with Deductions", Turbotax will tell you whether itemized deductions or the standard deduction provides you the most tax benefit.
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