In my contracting business, I've been "between jobs" quite a few times. There was a period when I was self-employed, and my wife wasn't employed (going to school) and I had to buy insurance on the open market.

Since my wife's condition made it very hard to insure her through normal channels, we went through California's high risk pool thing. It cost more, but at least she could get the policy, and we used that for a couple of years. State-supported high-risk pool insurance is a good example of how a local government can help with a health insurance issue with a relatively light touch, and without falling on the industry like a truckload of bricks.

Unfortunately, from what I've found so far, Florida does not have such a program open to new enrollees. I don't know why.

There are also HIPAA plans that will cover people with pre-existing conditions if their old insurance goes away and/or COBRA is exhausted. I don't know much about these things, but you might look into that, too.