Regarding #3, do you mean in the United States? That's not generally true. Your health insurance premiums, under normal employer plans, are not tax deductible, but they are paid pre-tax.
Additional out of pocket healthcare expenditure is only deductible if you itemize your deductions and you're only allowed to deduct medical expenditures in excess of 7.5% of your income (AGI to be technical).
Additional out of pocket healthcare expenditure is only deductible if you itemize your deductions and you're only allowed to deduct medical expenditures in excess of 7.5% of your income (AGI to be technical).