Comment by johnkpaul

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).