Jennifer: I am going to have a longer piece on Rudy Care early next week, so for now just a few brief comments.
Dubbing it "Milton Friedman Care" is way off the mark. That description implies that it is a big expansion of freedom in health care. But the only ways it expands liberty is by letting people without employer-based coverage have access to a tax break similar to the one that those with employer-based coverage do, and allowing people to buy health insurance out of state.
However, the second one comes with a big catch. You will be able to buy insurance out of state only if your state does not have health insurance policies that are "affordable." Thus, if you live in a state where the federal government has deemed that you have affordable insurance, you cannot purchase insurance out off state. That leads to the big problem of how to define "affordable." I don't know how they will define it, since the Giuliani campaign hasn't gotten that far into the details yet.
What I do know is that Milton Friedman would gag at the prospect of government defining something that should be a judgment left to individuals.