Q: My husband and I are within 6 months of making 23 years of frugal living payoff. Twenty three years ago, we moved to the Atlanta area with $2,000 cash to buy a house with, two children in college and an elderly mother-in-law to help support. We now have almost a quarter of a million dollars in cash assets (stocks, cds and bank accounts). Part of the stocks are in tax deferred accounts which we are slowly converting to taxable income. We have converted about half using real estate “paper losses” to even out the taxes due. I can quit teaching at the end of this school year but cannot draw my teachers’ retirement for two more years after that. We will be selling our primary residence for about $100,000 and will convert our rental property to a primary residence. We owe $30,000 on it. We will use part of the current property to finish updating the rental (we updated all mechanical systems while it was a rental).

My question is this: For the years between now and 65, what is my best bet for health insurance? I am incredibly healthy. The biggest health expense is one I am now incurring for dermatology and monthly trips to a chiropractor. My husband is on Medicaid (he had to take medical retirement 8 years ago and has been on my group insurance). He is still under treatment for a heart condition. Our youngest child is 18 and headed to college next fall with $25,000 and a paid for serviceable car. He recently had a hernia surgery but has been very healthy prior to that. I don’t yet know if I can convert my group policy since I am “quitting work” for the two years until I start to draw retirement. My retirement income then will be 4 times what we currently live on since we only live on a fourth of my after tax income. My husband’s social security is more than our living expenses. Any ideas about medical coverage for the three of us?

A: You can wait six months to resign, and then buy COBRA insurance coverage coverage. While it is expensive, it will cover you in the meantime. You might also check with AARP. You’re above the age limit for membership and you might be able to purchase less expensive coverage through them.

Medical insurance is expensive, but you’ll have the funds available even if you have to purchase full-blown insurance on your own. Look into HMO policies, and catastrophic coverage. The problem is not that you’re healthy. You’re 63 and hopefully you’ll live to be 93. The problem is that if you get into a car accident, or get hit by a bus tomorrow, or have a heart attack out of the blue (it happened to Jim Fix) or discover some other health emergency, you’ll be bankrupt in a year without health insurance.

Try COBRA, AARP and then talk to your insurance agent about medical insurance options. You might also try the web. Sites I like include Quicken Insurance. But off the top of my head, I can’t tell you if they do medical or not.

Congratulations on your frugality, and being able to retire when you’re in the prime of life. Enjoy your retirement — you’ve earned it.