When I became self employed in 2004 I kept the COBRA benefits as long as they allowed me to, but was unable to find replacement coverage at that point. I'm in reasonable health overall, luckily, but I'll be 50 this year, I'm kinda fat, and I have mild hypertension. Nobody I've asked - and I have looked for coverage - has been willing to issue me a policy. So I pay for my care myself, entirely out of pocket.

Note that this isn't a "too expensive" issue - I just get letters saying that they are unable to write me a policy.

I tried joining a small business organization that touts it's insurance pretty widely - they took my membership dues, charged me top dollar to get their "special" physical exam - and then sent me a refusal letter. Nearly 400 dollars later, I got a bunch of e-mail spam and a monthly newsletter for a year, but no health coverage.

My GP helps out with samples when I need meds - he's been my primary care doc for 25 years now - but for everything elseI'm in the scary position of paying my own way, exactly as you suggest.

I'm cool with it - hopefully good genetics will be my ally, and everybody dies some time - but this is definitely more than theoretical for me.