I’ve thought along similar lines in the past, but never with the urgency that seems appropriate now.
From what I’ve gathered, the sad fact is that if you have any income, you’re probably ineligible for most things.
However, there are some interesting ideas here: http://www.starvingthemonkeys.com/taxated/IncorporationTips.html
I’ve been thinking a lot about the above today, and I think there are several ways to make it work. The Cliff Notes version is that if you can become an independent contractor, even if to your current employer (assuming they’ll play ball), than a lot of costs become deductible expenses. You can also, if I read it correctly, turn a large personal income into a small personal income, plus a large corporate income, which would potentially make you eliglible for otherwise means-tested programs.
The big question, if you have health insurance through your employer, is how you’ll purchase whatever level you feel you need independently. That is probably going to be an ever-moving target over the next few years too.
If you work for a staffing agency as a contractor you can get insurance even though it isn’t as good as some insurances out there.