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Income-Related Documents:

Employed

  1. W-2 (Wage & Salary Income)

Unemployed

  1. 1099-G (Unemployment & State Refunds)

Daytrader

  1. 1099-B (Sales of stocks, bonds & other investments) from all Brokerage Firms
  2. Include .xlsx or .csv files for proper wash-sale calculations
  3. Day Trader Expense Deductions
  4. Entity Formation Documentation

Rental Income

  1. Income Statement (Records of Income & Expenses)
  2. Rental Asset Information 
    1. Purchase HUDs
    2. Sale HUDs
    3. 1099-S (Proceeds from Sale of Real Estate)
    4. Date Placed in Service
    5. 1098s – Mortgage interest statement
    6. Taxes & Insurance paid for each property owned

Self-Employed

  1. 1099-MISC (Self employment and other various types of income)
  2. Schedule K-1s (partnerships, trusts, S corporations or estates)
  3. Home Office Square Footage
  4. Income Statement for Business (Record of Income & Expenses)

Retirement Income

  1. 1099-R (Distributions from individual retirement plans, 401(k) plans, and other retirement saving plans)
  2. SSA-1099 (Social Security Benefits)
  3. RRB-1099 (Railroad Retirement Benefits)

Savings &  Investment Income

  1. 1099-DIV (Dividends)
  2. 1099-INT (Interest Income)
  3. 1099-OID (Original Issue Discount on Bonds)
  4. 1099-SA (Distributions from Health Savings Account)
  5. Record of Estimated Payments Made

Other Income Streams

  1. W-2G (Gambling Winnings)
  2. Alimony paid/received with Ex-spouse’s name and SSN

Deduction-Related Documents:

Home Ownership

  1. Form 1098 (Mortgage Interest)
  2. Real Estate Tax Bills
  3. Personal Property Tax, such as car registration

Charitable Contributions

  1. Support for cash donated to organizations
  2. Support for non-cash contributions 
    1. 1098-C (charitable contribution of vehicles)
    2. Clothing, furniture, etc. (ex – Goodwill receipt)
  3. Amounts of miles driven for charitable or medical purposes

Health Insurance

  1. 1095-A if you enrolled in an insurance plan through the Marketplace (Exchange)
  2. 1095-B and/or 1095-C if you had insurance coverage through any other source (employer, insurance company, government health plans such as Medicare, Medicaid, etc)

Other Deductions

  1. Amounts paid for healthcare insurance and to doctors, dentists, hospitals
  2. 1098-E (Student Loan Interest)
  3. 1098-T (Tuition for Higher Education)
  4. Child care Expense
  5. Amount paid for preparation of last years tax return
  6. Receipts for classroom expenses (educators K-12)

Bottom Line

If you can go through the list and gather as much information from here as you can you will be in great shape come tax time! Your CPA will let you know if they need any additional information. If you can provide a majority of this information ahead of time your CPA will be extremely grateful for your preparation during this busy tax time.