Ugh, I hate dealing with private insurance too. Why do they make it so hard to stay healthy?
I have a guy that I refer our clients to, who specializes in finding the lowest-cost private health insurance for people. His name is Robert Long and his number is ###-###-####. Give him a call and see if he can help you out at all. You should do whatever you can to get at least the most basic amount of coverage to protect your family if he starts accumulating a lot of medical expenses.
Also, I know the budget is tight, but if you don't already have some basic life insurance in place, you may want to start looking at that as well. Diabetes doesn't exclude him from getting life insurance, though it does limit the options a bit. If you need a referral for that as well, let me know.
Best of luck and congrats on the soon-to-be bundle of joy #2!