Let's talk about Democrat expectations for a moment by looking back to 2004. Initially the expectations were that Dean was going to win things in a walk. Why? Because the vocal minority and media were hitched to his bandwagon and doing all the pulling. But when it came time to actually vote we saw that the vocal minority was just that, and it was a much smarter, much more responsible, Democratic majority that was pulling most of the levers. They knew that raw, red, meat does not a dinner make, and they wanted someone who could offer more of an entree de' elegance for dinner and they went with Kerry.
With Republicans, you pretty much get what you see. Unlike Liberal Democrats, who tend to try to hide in the "Center" when they run, most Republicans can run pretty freely and openly on conservative issues. So, unless someone seriously falls on his or her sword, the most popular candidate stands a good chance of winning.
So, what can we learn? That at this stage of the game, the Democrat that's getting the most notice is often the loser, and the most popular Republican, baring any major goofs, will be the winner. I see Hillary as a loser in 08, along with Kerry and Gore if they're dumb enough to try a second bite at the apple, and Bayh wins the nomination. I see Condi and Cheney as the most popular Repubs amongst voters (and Rudi and McCain as the darlings of the media but not the voters), so I think that either of those two could easily win if they ran.
As for 2006, I think Hillary's going to have a tough row to hoe. Fazio was a last minute substitute with no name recognition, no real experience, no record, and he looked like a kid asking if he could please have some more... in short, he was a rotten candidate. Hillary was a woman with tons of name recognition and a celebrity, so she won. Now she's going up against another woman, who has a much better record of accomplishments than Fazio AND was a prosecutor, so she's not going to be all squemish about pressing Clinton for answers in a debate. I also don't see her backing down and playing nice for the media once Hillary starts her annual whining about being a victim of the VRWC. I can easily see her pressing the attack by saying that New York is a tough state and needs a tough senator, and if Hillary can't handle the heat she should get out of the kitchen, which will resonate with voters.
Lastly, what has Hillary done for New York over the past five years? What has she accomplished other than get her face on TV a lot? Nothing. Her fame let her get in the door in 2000, but I think most New York voters know that they need a senator who will get things done for New York first and an icon/figure head second. Plus they know Hillary is going to make a run in 2008, so they know she's just been using the state of New York as a springboard, which I don't see playing in her favor either. If there's every indication that the Republicans will hold the Senate I can see New York voters deciding to pick a senator who'll be in the majority and Hillary will be el' Toasted.