Since you are using the CD/Download TurboTax software, you do not have to upgrade in order to claim itemized deductions. TurboTax is recommending the upgrade, but it's not required. TurboTax Deluxe would give you a more detailed interview and additional help for deductions, but you can enter itemized deductions in Basic. It won't do any harm to enter them and see if they add up to more than your standard deduction.
