Yes, you can download Its Deductible more than once without it duplicating. I did it 2018 taxes. Upon receiving a letter from one of my charities, I saw 2 contributions that were not previously entered. I entered them on Its Deductible then went back to Turbo Tax, to deductions, then charity, then after a screen or two, the question about It's Deductible appeared again. I answered yes, logged in to it's deductible and the transfer was done a second time. It just updated the previous- it did not double the entries.
