Get your taxes done using TurboTax

@GeoffMather I just ran a test using $100,000 as a medical expense with both the TurboTax desktop editions and the TurboTax online editions.  It each case after completing the Deductions and Credits section of the program Itemized Deductions was shown as best for me.

Make sure that you have gone through the Wages & Income section and then complete the Deductions & Credits section. 

Also, if you are using the desktop edition make sure that you are at the latest release.  Click on Online at the top of the desktop program screen, click on Check for updates.