I think the key is to never let insurance lapse. Getting back on is the issue, I believe.
We have good coverage. My work does offer a retiree plan. Although, we will pay about 1300 a month. Ouch. It is a good plan though.
We will see what happens in 7 years. That should be our FIRE date. We may have to work 3 months or so a year just to pay the policies. My husband is an RN and we wants to maintain his license so that requires a certain amount of hours every year.
Even with the insurance monkey wrench, it does feel good to be on top of our finances. Almost debt free, two homes and a plan to build a third in a mountain biker paradise. Maybe our "retirement" may just have to look a little different by subsidizing. Being wise has allowed us to be semi fee by our mid our 50's. I see some people, poor health and still drudging along at work. This is due to their spending habits.