Hillary Clinton was not born yesterday, and neither were her politics or baggage.
First and foremost, she needs to say, "I'm not Bill Clinton," without insulting his fan base. How? I don't know. Bill's credentials are strong, yet he can also be the anchor that gets her stuck as a dead-end senator in NY.
Carpetbagger. We all know that she moved to NY to build her White House bid. Pretending just makes us look silly. Her path to returning to Washington was Park Ridge, IL (affluent suburb of Chicago), Little Rock, AK, Washington DC, then onto NY, and now, maybe back to Washington DC.
Then, she needs to not become "the female candidate." When Carol Mosley Braun ran as the first black female senator, she won, but then disappointed her supporters quickly on by a great show of incompetance. We all know Mrs. Clinton is smarter than that, but her handlers may not be. If she falls prey to that kind of thinking, she'll be pegged as just another wimmens libber, and no one right of left will vote for her.
Abortion. There. I said it. One of the dirtiest words in politics because there is no such thing as a real middle ground. Since Roe v Wade, there have been 47 million documented abortions in the USA, and Hillary is firmly on the pro-choice side. Those are hard numbers for mid- to right-wingers, since it represents roughly 1/3 of people in the USA under 30. It will be the younger crowd which first supports Hillary most fervently.
With abortion, she is in a rock and a hard place. Does she want to say "I am against abortion in all cases"? No, because that will pushaway much of the Democrats she needs to vote for her. Can she say something more middle-ground, "I'm against abortion in principle, but would not make it illegal"? No. She can't. If she does, she'll be claiming that abortion is somehow wrong (morally, ethically, or some vague "shouldn't be a contraceptive option"), and be, by default, telling those of her supporters who have had abortions that she supports their right to choose but thinks less of them morally. That will be seen as elitist. So what about the popular, "Abortion is wrong, except in cases of rape or incest, or if the mother's health is at stake," that will be, essentially, wimping out to the conservatives who claim the fetus' life value isn't based on the father (though they might accept the monther's health part.
Her solution to the abortion question should be to dodge it. If she's lucky, no one will look up her involvement or statements. This one needs to be blown passed as quickly as she can.
Iraq is too easy once she goes into the big November election, but getting out the primaries won't be easy. The solution will be to visit the Middle East a few times and say she's been there while her opponent has not been. If she ultimately runs agains John McCain, things get stickier, since his credibility regarding wartime is strong. In her back pocket though, she needs to be able to cite her plan for exiting Iraq.
Monica Lewinsky. This will be brought up. Monica will be interviewed as to which candidate she supports, and a lot of dirty politics will begin again. Jay Leno, Jon Stewart, Conan O'Brien and David Letterman are already working on this.
Whitewater. Does anyone care? Yes. The press. If the Monica story is going to slow, Whitewater will backwash into Hillary's run. Can she dry it out? How long ago was it?
As candidates go, she personally might be as scandal free as they come. As a woman, she was never a draft dodger. I doubt anyone suspects she has ever had an affair (insert laugh track here). However, presuming the press does not honeymoon her into office, and does due diligence when it comes to unveiling the past lives of all candidates, you never know.
Ideally, the race will be won or lost on issues and capabilities, not scandal. There are plenty of real issues to talk about.