I plan to itemize this year because I have about $17K in gambling wins. I've also lost quite a bit and plan to offset the wins with losses. I know how to enter the wins in the software, however, where to I enter the losses?
You'll enter your gambling losses under 'Deductions/Credits' > 'Other Itemized Deductions'.
Please note that the option to deduct your gambling losses will only appear on that screen after you've entered your gambling winnings under 'Income' > 'Gambling Income (W-2G)'.