I have a question regarding how to enter out of pocket medical expenses and with a Health Savings Account.

If you have a Health Savings Account (HSA), you should receive form 1099-SA.  First enter the information about your HSA distributions (reported on the 1099-SA) and then enter the medical expenses you incurred during 2016.

Here's how to enter your 1099-SA form:

1. Click on Federal Taxes > Wages & Income    [In TT Self-Employed:  Personal > Wages & Income > I'll choose what I work on].
2. In the Less Common Income Income section, click on the Start/Revisit box next to 1099-SA, HSA, MSA.  [See Screenshot #1 below.)
3. Continue through the interview, entering the information contained on your 1099-SA.

To enter medical expenses in TurboTax, please follow these steps:

1. Click on Federal Taxes > Deductions & Credits  [In TT Self-Employed:  Personal > Deductions & Credits > I'll choose what I work on].
2. In the Medical section, click on the Start/Revisit box next to Medical Expenses.  [Screenshot #2]
3. Continue through the interview, entering the requested information on your medical expenses.
4. You will be asked to confirm the amount you withdrew from your HSA/MSA to pay for medical expenses.  TurboTax will then calculate your medical expenses deduction.