Would I fund an HSA with pre- or post-tax dollars?

If your employer offers a high-deductible health insurance policy, you may be able to make pretax contributions, like you would with a flexible-spending account. If you open the HSA on your own, your contributions will be deductible when you file your taxes, even if you don't itemize.

You can now deduct your contributions up to the $3,050/$6,150 limit -- plus an extra $1,000 if 55 or older -- regardless of the size of the deductible.