meesterj,
There is a bigger picture you need to keep in mind. The total of all your itemized deductions has to exceed your standard deduction to be of any value. For the federal return, the main itemized deductions are (a) charitable contributions, (b) state income tax (or a sales tax alternative), (c) property taxes (up to a $10,000 limit), (d) mortgage interest (up to a certain limit), and (d) medical expenses (including health insurance you pay for) that exceed 7 1/2% of your adjusted gross income. You would compare this to your standard deduction amount of $12,950 for single filers, $25,900 for joint filers, or $19,400 for head of household. (There are additional boosts for blindness and senior citizens.)
I volunteer with AARP and a companion VITA program preparing taxes and have yet to see a taxpayer with enough itemized deductions to exceed their standard deduction.
The story can be different for state income tax purposes. For example, in California you can choose to itemize on the state return without itemizing on the federal on. That state's standard deductions are $5,202 for single taxpayers and $10,404 for married and head of household. You cannot use the state income tax or sales tax with California, but all the others count plus a few more miscellaneous ones.
