Obviously the Dems strategy this year is to link McCain to Bush, and use an unpopular presidency to drag down McCain's popularity. There is a certain amount of irony to this since Bush and McCain have been political rivals for quite some time; and that in 2000 McCain was targetted by Bush and Rove and particularly dirty and underhanded way. However, the stategy remains to connect these two in the eyes of the public.
However, a more substantive comparison would be Obama 2008 and Bush 2000. There is a similarity to their campaigns. 'A uniter and not a divider' is the 2000 version of, 'Yes we can'. They both ran on a platform of change, and the most glaring similarity is their utter lack of experience. Bush and Obama made claims that their inexperience made them outsiders capable of chaning 'business as usual' Washington. Bush didn't know who the president of Pakistan was, Obama guaranteed to meet with Ahmedinejad in the first year of his presidency without preconditions. Both statements made their campaigns and supporters wince and bite their nails. Their success despite their lack of substantive discussion of issues, was marketted as refreshing and new. The guy we'd have a beer with, shoot hoops with, but not neccessarily the guy we'd trust to do our taxes. Finally, both marketted experience as a negative. The Obama campaign tags Clinton and McCain as relects of a failed Washington just as Gore was tagged as a with the negatives that President Clinton carried. Conveniently skipping over the knowledge that is attained through experience. Consequently, these two excellent campaigners are rewarded for being totally unprepared to run the country.