"Normally", any payments that you make towards your health insurance plan that are done by a salary reduction/payroll deduction plan are indicated by a code "DD" in box 12 on your W-2. This amount will also include what your employer puts towards your health insurance premiums.
In the same way, contributions to a retirement plan done through a salary reduction/payroll deduction plan are indicated by a code of "D" in box 12 on your W-2 (this is for a 401(k) plan).
In either case, these amounts are pre-tax, that is, they are removed from Wages in box 1 on your W-2.
Therefore, you don't need to enter them anywhere else on the return; TurboTax will handle them automatically.
The real issue is "are these contributions pre-tax"? If they are, you don't normally enter them anywhere else once you have completed your W-2.
As for the insurance reimbursement, on Schedule A, TurboTax expects you to list all medical expenses that you paid, and then it will ask you towards the end how much you were reimbursed. Add your foreign reimbursement there. TurboTax will then net the reimbursements against the payments to see if you qualify to take any medical deductions on Schedule A.
