You have my utmost respect and awe too.
I don't have advice on the insurance side of those questions that hasn't already been given but I do about the issue of time that you brought up. I love being a SAHM and strongly recommend going that route too. I remember worrying about my time, my kids' time and my sanity too when I quit work but somehow there is so much to do and so much fun to have with the kids that it seems like a much less trivial thing to worry about (time that is).
Now, having said that, I know dozens of moms who find other smaller jobs at home or where they can take their kids who do that on the side too. There are lots of jobs out there. Anything from teaching lessons or tutoring to cutting out fabric for design stores to daycare at athletic clubs. There are many other things to do to enhance your income and find a suitable social outlet that works for your kids.
The job I left was a teacher. I totally believe you when you say that 1/2 your salary is for child care. That's only half the story. The other half is the time it takes to be a teacher. I don't care how experienced you are it just always takes more time outside of the classroom to prepare than the rest of the world thinks it ought to. Between time and money, is it really worth it? I didn't think so. Best of luck on your decision.