I joined the ranks of the uninsured last year when I entered the 55+ band and my small business group insurance rates jumped $500 per month to $1,200 per month with a $5,000 deductible. I could no longer justify the cost of that insurance. I would have to pay $19,400 out of pocket before getting one cent of coverage. I do carry a supplemental plan through AARP, but couldn't even qualify for individual health insurance through AARP's insurer with my pre-existing conditions.
I was in a small business group pool in Florida when I saw this outrageous price jump. Florida's small business pool does include anyone who files a Schedule C and runs a business, even if that business only has one employee. I'd gotten my insurance through this pool for three years prior to dropping it.