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You are posting from the Free Edition, which will not support itemized deductions, so if you are going to enter itemized deductions you need a higher paid version of the software. Before you upgrade, take a close look at what you will be able to enter. With the new increased standard deductions, it will be hard for many people to use itemized deductions.
Charitable donations do not count "dollar for dollar," Your charitable donation deduction is calculated by a percentage based on your tax bracket. You need a LOT of other itemized deductions like mortgage interest or property taxes, medical expense, etc. to itemize and exceed your standard deduction. Medical expenses must meet a tough threshold before they can have any effect at all.
MEDICAL EXPENSES
The medical expense deduction has to meet a rather large threshold before it can affect your return. The amount of medical (including dental, vision, etc.) expenses that will count toward itemization is the amount that is OVER 7.5% of your adjusted gross income. You should only enter the amount that you paid in 2018—do not include any amounts that were covered by insurance or that are still outstanding. Of course, your medical expenses plus your other itemized deductions still have to exceed your standard deduction before you will see a difference in your tax due or refund.
To enter your medical expenses go to Federal>Deductions and Credits>Medical>Medical Expenses
2018 Standard Deductions:
Single $12,000 (+ $1600 65 or older)
Married Filing Separately $12,000 (+ $1300 65 or older)
Married Filing Jointly $24,000 (+ $1300 each spouse 65 or older)
Head of Household $18,000 (+ $1600 65 or older)
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