A Republican at work had a discussion with me about his theory that the Clintons are trying to ensure Kerry doesn’t win. (I think his theory is bogus.)
He claims that they are positioning Hillary to run and she would have run this time had she known the swing against Bush would be so strong.
I think if Hillary were running for President today, it would be about the same as Kerry - meaning, I think she could win, and would win.
So - I don’t see being a woman being a minus in an election, but it depends on the woman and I think Hillary could pull it off.
That said, I think Colin could also have run, and still run, a serious campaign. Even someone like me, a rabid Democrat, would not feel the need to open a vein if Colin won.
In other words, there are candidates who fall in both of your catagories who could win the election. It is a matter of time, and timing.