A Checklist to be Ready to File

No matter how you decide to prepare your taxes, you’ll need to assemble all the documents needed. Having them available will make the entire preparation process much easier.
The most basic information you need to have available includes:

• Social Security numbers for each member of your household
• Complete copies of the prior year’s income tax returns (you’ll need these to provide any carryforward information)
• Income information for your dependent children
• Home office information (if you plan to take the deduction) – square footage of your office, and of your home
• Your ex-spouse’s Social Security number if you receive or pay alimony or child support
• Marketplace exemption certificate, if you received an exemption from your state’s health insurance exchange

Income documentation includes the following:

• W-2s from any employment sources
• 1099-MISC for additional income for which income taxes were not withheld (like contract income)
• 1099s reporting Social Security income, interest and dividends; pension, IRA or annuity income; state income tax refund or unemployment insurance; or reporting the sale of stock or other securities
• K-1’s reporting partnership or S-Corporation income
• W-2G reporting gambling winnings (you should also have records proving gambling expenses)
• Documentation of alimony received, including the social security number of the payee
• If you’re self-employed, a complete accounting of all your business income
• Evidence of rental income received, if you own investment property

A Documentation Checklist for Tax-deductible Expenses

Potentially tax-deductible expenses are reported on the following documents:

• 1098 reporting mortgage interest and property taxes paid, educational expenses, and student loan interest paid
• Statements from charities reporting contributions
• 1095-A, 1095-B, or 1095-C, reporting health insurance premiums paid, and to whom
• Various forms 5498 reporting IRA, HSA or ESA payments made during the year.

There are a lot of situations involving tax-deductible expenses, that are not neatly reported on a government form from third-party sources. You may need documentation for any the following expenses:

• Documentation of all self-employment expenses
• Expenses for rental property
• Documentation for the purchase of depreciable assets for business or investment activity
• Property taxes paid but not reported on Form 1098 by a lender
• Federal and state estimated tax payments made for the tax year
• Cost basis of investments sold (if the information is not provided by a broker)
• Indirect expenses related to investment activity
• Documentation of alimony paid
• Receipts from the purchase of energy efficient equipment installed in your home
• Charitable contributions made but not reported by the receiving organization
• Mileage driven for business, employment, medical or charitable activities, as well as records of payment for tolls, parking and ad valorem taxes
• Evidence of payment of health insurance, out-of-pocket medical, dental and vision expenses, medical mileage and long-term care insurance
• Childcare expenses paid, if not supplied by the provider (including the provider’s tax id number)
• Wages paid to a domestic care provider, including that provider’s tax ID number
• An itemized list of higher education expenses paid out-of-pocket, with documentation
• Moving or job hunting expenses
• Cost of preparation of last year’s income tax returns
• Sales tax paid on major purchases