Although what almost hurts me more is that JK was swiftboated twice. The first time was in 2004, where the media treated the official NAVY record as having less credibility than men, allied with Bush, caught in one lie after another. The media condoned a character assassination. With Obama, the comparable thing is that the media continues to give air to birther claims. In both cases the official record is completely unambiguous. Obama has it a bit easier as in his case the truth is simpler and few in the media give any credence to the birthers. The second time started as soon as he lost. To their eternal discredit both the Edwards and Clinton people pushed the story that Kerry did not respond or responded weakly.
In the case of the Edwards people, it was despicable. Kerry gave that vain egotistic guy a shot at being VP and he was a VP from hell, not defending Kerry when asked and telling the media he was too good for that role and refusing to even use the Kerry slogans. He then had the chutzpah to say that he told Kerry that Kerry had to fight back.
In the case of the Clinton people, their goal was to foster the idea that only Clintons really know how to fight the right wing. This ignores that the vaunted "war room" actually did less than Kerry did - partially because the attacks on Clinton contained some truth - and in Kerry's case, he was the war hero the Navy records show. The Clinton people used that theme against both Gore and Kerry and implicitly anybody not them. It happened often enough that I kept cutting and pasting the same response - tailoring it slightly every time it came out. Here's a recent version -
http://www.dailykos.com/comments/925822/39278676 (In all honesty I now have two reasons for countering it on DK - one is that it still needs to be hit and the other is that now it gets lots of recommends and helps me sometimes be a trusted user with little work.
In addition to all you list, 2004 was tougher because whoever won would select 2 or 3 Supreme Court justices, including Rehnquist. This meant the abortion issue was far more powerful. The Catholic church took a much larger role and so did some evangelical groups, A Democrat would have seriously changed the direction of the court. But, looking back now, I also see that corporate interests would have had no chance getting the Citizens United decision from a court where Roberts and Alito would have not been there and two JK judges would be there. (I think this would have been the case even if JK were not re-elected. I suspect that Stevens or Bader Ginsberg would have retired earlier rather than risk the Repuublican winning.) That decision had a major impact on 2010.