How to report health insurance premiums that retiree paid directly to providers? Paid extra to cover federal & state income taxes? 1099R is not complete

If you are paying Medicare premiums directly from Social Security benefits, and you enter all of the information from your Form 1099-SSA in the Wages & Income section, TurboTax will automatically record the premiums paid in the Medical Expenses section of Deductions & Credits. Premiums paid through OPM retirement or other retirement plans may not be automatically transferred.

Visit the Medical Expenses section of Deductions & Credits to enter any medical insurance premiums you paid that weren't automatically transferred from the entries in another form.

You can preview your return before filing to review the forms that TurboTax has prepared from your entries and to find out how your taxes were calculated. See here for details. 

You will only be able to get a deduction for Medical expenses if the total of these expenses exceeds 7.5% of your Adjusted Gross Income. For example, if your AGI is $50,000, the first $3,750 of qualified expenses (7.5% of $50,000) don't count.

See this article for more information regarding deductible medical expenses.