The rule of thumb is that you always want to pay for benefits with non-taxable dollars. If you pay for them with taxable dollars, then when you get the benefit, you have to pay taxes on that benefit. Taxes on premiums are always cheaper than taxes on benefits. The best example is life insurance: the premium on a life insurance policy is a few dollars a year (depending on what the premium is and your tax bracket) but that is certainly cheaper than paying taxes on a life insurance benefit of $50,000 or $250,000! Other examples include disability policies and benefits and long-term care.
Health insurance and its related health savings accounts are not, by law, taxable (as of when this post is written). In fact, employee payments for both health insurance and HSAs are tax-deductible and employees should be encouraged to max out their HSA amounts if financially possible (same goes for retirement).
Lead On!