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I'll try to answer some of your questions, but others may be better than I at explaining things.

1. Only itemize if you can take over the standard deduction. Since you are single, that is over 4700 dollars. From what I see, you may be borderline for single. And you wouldn't make it at all if you're married. Usually itemizeing only works if you have a mortgage or a boatload of medical expenses.

2. Student loan interest is off of gross on the front of the 1040. So take as much as you can.

3. As for the tuition, run the numbers, but Lifetime Learning comes off the tax, dollar for dollar. Almost always this is better than reducing gross.

4. Parking is subject to the 2 percent of AGI. In your case, 2% of 37783 is around 756. Your parking is only 570. If your AGI comes out to 24813, then it's 496 and the parking is just barely deductible.

5. The tornado loss (wow, what bad luck!) is reduced by 100 dollars and then by 10% of AGI. So probably not deductible.

6. Don't know about the 403b and IRA limits, the people I see to do taxes for rarely contribute to such things. Need all their money just to pay bills.
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