It may sound a little racist, but I think Obama's liberality has always been hobbled by his race. He couldn't act freely because he always had to be sensitive to the average voter's racist tendencies. That's why he gave in so easily to "whatever Congress comes up with" as the ACA. That's why he has been so passive about the Republicans doing everything in their power to defeat anything he approves, even if their actions border on treason.
As I recall, he wanted a public option and the best the Congress of the time could pass was the totally Big Health Insurance and Big Pharma thing we have now. I don't think Hillary is going to "tread lightly" because she is a woman. In fact, I think she is going to do a bit of extra stomping when it comes to Congress. Anybody who attacks her personally is going be singled out to feel some pain, like maybe being defeated in the next election, indicted for past crimes, etc.
