Are there specific records I need to keep?

By Jason Watson (Google+)

Yes.  The IRS lists several items in Publication 552 which include alimony, casualty losses, charitable donations, child care, education, gambling, home office deductions, IRAs, job-related expenses, medical, mortgage interest, moving expenses, pensions and annuities, sales tax on vehicles and tips.

Each item has specific requirements. For example, casualty losses and thefts require that you can demonstrate that you owned the property, that you were the named insured of the property, and that the loss occurred during the tax year of the deduction. With just that in mind, you need to keep insurance information such as a declarations page and the police report. Geez!