For the question "Any contributions you personally made (not through your employer)" in regards to the HSA & have box 14 HSA filled in on your W2 do you put that number?

This question is asking if you made any contributions independent of your employer. You employer would not know about any contributions that you made on your own. An employer can put anything in Box 14.

On your W-2, the Box 12 code W amount includes both the employer and employee contributions. If you contributed to your HSA only through payroll deductions, do not enter them anywhere else in TurboTax.

On your HSA summary page, you will see Tax-free employer contributions, but it means both employer and employee contributions in total. It is just how the IRS codes Box 12.

However, if your made after-tax contributions on your own (independent of your employer), then those contributions would be entered in the Medical section. You would have to enter them to calculate a deduction and complete Form 8889 properly.