Gandalf,
Glad to hear that story as it validates one of the things I definitely was trying to accomplish, having the book work both for someone in the planning/pre-ER stages and in the semi-retirement or early retirement stages, too.
Hillbilly, you're right on target and health insurance is going to get a lot more treatment in the next edition, but it's a vast field, with slight differences state by state, to say nothing of the issues for FIREes in other parts of the world.
In the options you were considering, have you talked to a local insurance broker? They shouldn't cost you anything extra, since they get paid by the insurance companies, whose rates are set by law, so it isn't like hiring an expensive financial advisor. They may help you see through the thicket of choices. A few ideas that came to mind that I didn't see on your list: just paying COBRA for 6 months after leaving your job, and then going into your state's high-risk pool? (or do you literaly have to be uninsured to get into your state's pool? that would seem odd). Or what about High-deductible plans, where you just assume you'll probably have to pay the full deductible each year out of your linked HSA?
HIPPA, if I understand correctly, lets you transfer to another plan without excluding your pre-existing conditions for a period, but the trick of course is, which plan would you be able to qualify for. That's where some more creativity might help -- employer-based plans are often treated better than individual plans. But you can be a group of 1 now. Think about starting a little side self-employment company, even while you work, with an eye toward having this company start a group plan for you. Could be a good way to segue into semi-retirement, too, doing some consulting in your current field or making a hobby into a business with a small income stream.
Finally, if you're willing to consider moving out of the country as a last resort, what about considering moving to another state in the U.S.? Some states have pretty congenial guaranteed issue provisions. Your pre-existing conditions might not be covered right away, then again, HIPPA might ensure they are if you go straight from one plan to another-- their big worry seems to be uninsured people who suddenly see the light and want to get insurance when they are diagnosed with a major illness. If you stay insured, I think you're in better shape for having the pre-existing condition covered. In any event, I would certainly never recommend you go 'bare', and have trouble seeing scenarios where you would somehow be rewarded for doing so by being able to get new or better insurance -- is our system really that contorted that those incentives now exist?
Anyway, I'm going to get all these issues into the next edition, but if anyone has more thoughts on this, or corrections to anything I've written here that you think I'm misunderstanding or which wouldn't apply in your state, I am all ears, as there is a lot to learn. Anybody have any experience asking an insurance broker for help in getting coverage around the time of FIRE? My experience is that the corporate plan guys are better than the individual plan guys, but you might need to have a self-employment company started first. Having said that, I also have been burned by a fraud with a corporate guy who sent a post-card, so caveat emptor. Maybe best to ask a small business person who their insurance broker is, rather than just answer an ad.