RE Insurance:
Yes, you are betting against yourself - with the whole of the "group" as a base - the insurance company will NEVER (or almost never) lose against the group as a whole

An individual can occasionally "Break the Bank" (unfortunately, over the last 12 months, I've been one of those)

Generally - if you can't get seriously discounted medical (hey, my company pays for it, and won't give me more pay if I opt out, so I might as well 'play' - as I'm playing with 'funny money'), you are best off with a pure "catastrophic" plan. At one point, we had a plan - basically it covered NADA till something like $10K. The way it worked - it was basically "if you get in an accident/have something drastic happen (cancer, heart attack etc), we will pay after you rack up 10K in bills" - wan't cheap, but wasn't too expensive either. The KNEW I was not going to be submitting anything unless I/my family was in the hospital dieing
73 de KG2V
You are what you do when it counts - The Masso