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As far as the insurance premiums go, they would only be deductible if paid after tax is withheld If the payments lower the amount in Box 1 Gross Wages, then they are not deductible because you have already received the benefit of earning that amount of money tax free.
For the medical expenses, they may be deductible if you itemize deductions, but the only part that is deductible is the amount over 10% of your Adjusted Gross Income for the year. So if your AGI is , say, $50,000 you would only get a deduction for the expenses over $5000.
Even then, you only itemize if the total of all your itemized deductions exceeds your standard deduction of $12, 600 for a married couple.
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