Caroline Kennedy to Senate?
The main drawback is that Kennedy is not what you'd call highly qualified. She's a public servant of sorts -- she's run some commissions and funds and is Honorary Chairman of the American Ballet Theatre. She's written a surprising number of books. But she has mainly avoided politics and even turned down the chair of the Democratic National Convention in 1992, which would have been a natural way to get in.
On the other hand, she has campaigned for politicians, so she has some idea how the sausage is made. And we already have some Senators who came in without traditional political experience, including Jim Webb and Clinton herself, though the Junior Senator from New York's thin record of accomplishments (particularly in relieving the upstate economy) reminds us that not every fast riser is Abraham Lincoln.
Not that it matters. In 1999 former Senator Alan Simpson told Time magazine Kennedy had "poise and warmth and [a] desire to participate in politics and carry on the Kennedy name." He was wrong about the politics, but for the clubby atmosphere of the Senate, maybe poise and warmth are meaningful recommendations.