Should I take the HSA health insurance option? When used properly, 9 times out of 10 the answer is a resounding YES! Here is a readable article from Kiplinger on 5 HSA Benefits. Of particular interest for some is Benefit #5 – Closing the Retirement Gap. For those that are able to cash flow max funding their HSA and paying (and keeping receipts for) their out of pocket medical expenses with after tax dollars each year, using an HSA as a long-term retirement account can rival even a matching company retirement plan!