I tried both of the free tax filing options the IRS.gov website offered me: Turbotax and FileYourTaxes.com
Turbotax was more intuitive, as it calculated my itemized deductions by asking me about them. FileYourTaxes simply showed me Schedule A and suggested I fill it out.
However, when it came time to file, "free" Turbotax wanted a $39 upgrade to actually file the Schedule A, whereas FileYourTaxes did it for free.
I'm not going to tell you what to do, but you might start with Turbotax. If it recommends you use your standard deduction, fine, but if it recommends you itemize and asks for your money, run FileYourTaxes in a new window and copy the itemization information that Turbotax calculated for you.
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