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Expenses that May Qualify
for Itemized Deductions

 To be eligible, the expenses must have been paid during the tax year.  Proper documentation is required in order to take any deduction. 
It takes approximately $1000 in itemized deductions to reduce your taxes $100.

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Comments on this website are informational in nature and are not intended to
be interpreted as specific tax advice.   The comments cannot be used to avoid taxes under the Internal Revenue Code or the regulations of other tax authorities. Furthermore, this website is not intended, and should not be interpreted, to support the promotion or marketing of any tax avoidance schemes.


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  • Home Mortgage Interest
  • Home Equity Loan Interest
  • Some Mortgage Refinance Expenses
  • Some Investment Interest Expenses
  • Credit Card, Auto Loan, IRS and State Tax Interest are not deductible


  • State/Local Income Taxes
  • Real Estate Taxes
  • Personal Property Taxes
    (part of registration fees for motor homes, campers and travel trailers)
  • Sales Tax, when not claiming State Income Tax
  • Tax penalties are not deductible

Out-of-Your-Pocket Medical (only a portion will be deductible)

  • Doctor/Dentist Fees and Co-pays, includes chiropractic, acupuncture, naturopath, nurse practitioner, etc.
  • Hospital Fees/Co-pays
  • Prescription Drugs
  • Insurance Premiums, including long-term care insurance, paid with after-tax dollars.
  • Lab/X-ray/other medical tests
  • Glasses, Contact Lens, Hearing Aids, Dentures, Medical Equipment, some medical comfort items required for patient care
  • Nursing, Convalescent and Home Care payments when medically necessary
  • Certain tuition costs for children with medically-diagnosed disabilities when the main reason is to overcome the disability.
  • Mileage to and from medical appointments; also parking and tolls. 
  • If you are over 64, Oregon allows a special medical deduction for some taxpayers.

Some Casualty and Theft Losses

  • A portion of the loss not compensated by insurance may be deductible.
  • Stock losses are not a theft loss even if corporate officers are convicted of wrong-doing.  In some cases, worthless securities might be deductible as a capital loss.
  • Considerable documentation is required to support the deduction.

Some Political Contributions

  • Tax Credit on Oregon returns only, not federal.  You must have a receipt or letter to verify the contribution.
Charitable Contributions
  • Cash and non-cash donations to IRS-recognized non-profit organizations (search IRS website for "Exempt Organization Select Check" tool); receipts, bank records or letters from the recipient organization are required for ALL donations regardless of the amount donated. 
  • Single gifts over $250 must be acknowledged by a letter from the charity.
  • Non-cash gifts may include clothing, household items, merchandise purchased for donation, etc.  The donor must determine a reasonable value for the contribution.
  •  Use this guide to assign values. Ask for a receipt from the receiving organization.  Some high-value items, such as cars, antiques, paintings, jewelry, etc., may require an outside appraisal.
  • Mileage to and from volunteer activities . 
  • Unreimbursed volunteer expenses
  • No deduction for time spent volunteering. Parochial school tuition is not considered a charitable contribution.

Miscellaneous Expenses (only a portion will be deductible)

  • Union & Professional Dues
  • Tax Preparation Fees
  • Safe Deposit Box Fees
  • Some Investment Expenses/IRA and Trust administration fees
  • Some Unreimbursed work expenses (overnight travel, uniforms, tools, phone, etc.)
  • Some Job-related Moving Expenses; qualified mileage is deductible.
  • Professional/Trade Expenses (professional journals, conferences, memberships, licensing, etc.)
  • Some Job-seeking Expenses
  • Some Job-related Continuing Education Expenses
  • Gambling Losses to the extent of Gambling Winnings claimed as income.
  • Unreimbursed business mileage Commuting mileage is never deductible.
  • IRS expects you to keep a mileage log to document mileage claims.  Your appointment calendar can be the base for a mileage log.
  • Unreimbursed business expenses must be considered necessary and standard to your  industry and your employer must not offer reimbursement for expenses incurred per company policies.  Documentation must include receipts, an appointment calendar and the business purpose of each expense.

REMEMBER, in a tax audit, you are responsible for proving you are entitled to take the itemized deductions on your return.,