Health Insurance Options
My wife and I founded and grew a very successful tech company over the past 10 years and we just had our exit. We have done several property flips and have a few rentals that we’ve accumulated over the years. We really enjoy investing in real estate and will be doing a combination of syndicate deals, commercial buy and hold and residential (if the market ever cools).
We had hundreds of employees at our previous business and we had fantastic health insurance for our family. Our son was recently diagnosed with a chronic condition that requires very expensive ongoing treatment.
What do the passive investors out there do for health care coverage? I know we can look on the healthcare exchange but I’m told those plans are pretty terrible. What creative options are out there?

My family uses a plan on the healthcare exchange - and it works for us. I think finding a good plan is like so many other financial things - the quality of your solution is directly related to the quality of the advisor/agent/professional who helps you with the solution. I have a very thorough and diligent agent and he shopped around until he found the most affordable and comprehensive coverage available for my family.
Another option that I looked into is using my real estate LLC to join the Chamber of Commerce and then you can access the health plans that they offer to small businesses. For now, the regular healthcare exchange was better for us.

Passive RE investor and health insurance advisor here.
Sorry to hear about your son's situation. I'm a father for the first time, got a 2-year-old son and I can't imagine what that must feel like if he ever got sick like that.
In my opinion, private health insurance is the best way to go if you are self-employed. They have similar rates as ACA (marketplace) but better coverage (ex: PPO network). However, there is an underwriting process and NOT everyone can qualify.
Happy to share more if it's helpful.

I've had a few friends who've been in similar situations after selling their companies. Many of them joined professional or industry associations for healthcare, which often have group plans that are a bit more robust than what you might find on the standard exchanges.

Another popular option has been setting up a Health Savings Account (HSA) combined with a high deductible plan; this could offer some tax advantages.
Considering your son's situation, it might be worth checking out Medicaid. It might seem odd, but Medicaid Florida has different eligibility requirements and income limits. Perhaps that healthcare plan could be more advantageous for your family and may assist with your son's condition.

We use Christian based medi-share. We are healthy in our 50s(Me) and 40s(Wife) and selected the higher deductible. The cost is just over $300 per month for us